1-(2,5-dimethoxy-4-methylphenyl)propan-2-amine [DOM] by Asch

Reaxys

PubChem

eMolecules

Reactions (60)

Substances (17)

Citations (124)

Structure

Structure/Compound Data Chemical Name: (+)-DOM Reaxys Registry Number: 475988

CAS Registry Number: 43061-14-9 Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H19NO2

Molecular Weight: 209.288

InChI Key: NTJQREUGJKIARY-VIFPVBQESA-N

N° of preparations All Preps | All Reactions

Available Data

N° of ref.

11 prep out of 14 reactions.

Identification Physical Data (1) Bioactivity (5)

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+)-DOM, (S)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane, (S)-(-)-2,5-dimethoxy-4-methylamphetamine, (S)-2,5-dimethoxy-4methylamphetamine, (+)-3-(2,5-Dimethoxy-4-methylphenyl)isopropylamin Identification Substance Label (5) Label

Reference

(S)-5b

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

(S)-(+)-DOM

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

McGraw, N. Peter; Castagnoli, N.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

12a

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Derivative (1) Comment (Derivative) Hydrochlorid: F: 204-205grad;

Reference <α>(D)25:

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

+17.2grad

Purification (1) Purification (method)

Reference

(+)-2-nitro-tartranilic acid

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Physical Data Association (MCS) (1) Description (Association (MCS))

Partner (Association (MCS))

Solvent (Association (MCS))

Temperature (Association (MCS))

Stability constant of the complex with ...

cytochrome P-450 (microsomal protein)

various solvent(s)

31 °C

Bioactivity Pharmacological Data (5) 1 of 5

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

McGraw, N. Peter; Castagnoli, N.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048

Reference McGraw, N. Peter; Castagnoli, N.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

Title/Abstract Full Text View citing articles Show Details

Gal; Gruenke; Castagnoli Jr.

Journal of Medicinal Chemistry, 1975 , vol. 18, # 7 p. 683 - 688 Title/Abstract Full Text View citing articles Show Details

McGraw; Callery; Castagnoli Jr.

Journal of Medicinal Chemistry, 1977 , vol. 20, # 2 p. 185 - 189 Title/Abstract Full Text Show Details

Gomez-Jeria; Cassels; Saavedra-Aguilar

European Journal of Medicinal Chemistry, 1987 , vol. 22, # 5 p. 433 - 437 Title/Abstract Full Text Show Details

McGraw; Castagnoli Jr.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

2 of 5

3 of 5

4 of 5

5 of 5

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant human TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1

Results

no effect (related to human TAAR1)

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant rhesus monkey TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1; effective concentration (EC); EC50 related to: monkey TAAR1

Type (Pharmacological Data)

EC50

Value of Type (Pharmacological Data)

0.9 μmol/l

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant rhesus monkey TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1

Results

molecular target: monkey TAAR1

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

serotonin binding affinity in the rat stomach fundus

Reference

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (-)-DOM Reaxys Registry Number: 475989

CAS Registry Number: 43061-13-8 Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H19NO2

Molecular Weight: 209.288

InChI Key: NTJQREUGJKIARY-SECBINFHSA-N

13 prep out of 16 reactions.

Identification Physical Data (1) Bioactivity (4)

Synthesize | Hide Details Find similar Chemical Names and Synonyms (-)-DOM, (R)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane, (R)-(-)-2,5-dimethoxy-4-methylamphetamine, (R)-2,5-dimethoxy-4methylamphetamine, (-)-3-(2,5-Dimethoxy-4-methylphenyl)isopropylamin Identification Substance Label (5) Label

Reference

(R)-5b

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

(R)-(-)-DOM

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

McGraw, N. Peter; Castagnoli, N.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

11a

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Derivative (2) Derivative

Comment (Derivative)

Reference Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

(-)-DOM hydrochloride

Hydrochlorid: F: 204-205grad; <α>(D)25

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

Purification (1) Purification (method)

Reference

(-)-2-nitro-tartranilic acid

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Physical Data

Association (MCS) (1) Description (Association (MCS))

Partner (Association (MCS))

Solvent (Association (MCS))

Temperature (Association (MCS))

Stability constant of the complex with ...

cytochrome P-450 (microsomal protein)

various solvent(s)

31 °C

Reference McGraw, N. Peter; Castagnoli, N.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (4) 1 of 4

2 of 4

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Univ. Iowa

Patent: US4000197 , 1976 ; Chem.Abstr., vol. 86, # 139599 Full Text Show Details

McGraw, N. Peter; Castagnoli, N.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

Jacob; Nichols

Journal of Medicinal Chemistry, 1982 , vol. 25, # 5 p. 526 - 530 Title/Abstract Full Text View citing articles Show Details

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Deeb, Omar; Clare, Brian W.

Chemical Biology and Drug Design, 2008 , vol. 71, # 4 p. 352 - 362 Title/Abstract Full Text View citing articles Show Details

Matin; Callery; Zweig; O'Brien; Rapoport; Castagnoli Jr.

Journal of Medicinal Chemistry, 1974 , vol. 17, # 8 p. 877 - 882 Title/Abstract Full Text Show Details

Gal; Gruenke; Castagnoli Jr.

Journal of Medicinal Chemistry, 1975 , vol. 18, # 7 p. 683 - 688 Title/Abstract Full Text View citing articles Show Details

McGraw; Callery; Castagnoli Jr.

Journal of Medicinal Chemistry, 1977 , vol. 20, # 2 p. 185 - 189 Title/Abstract Full Text Show Details

Glennon; Raghupathi; Bartyzel; Teitler; Leonhardt

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 Title/Abstract Full Text Show Details

McKenna; Peroutka

The Journal of neuroscience : the official journal of the Society for Neuroscience, 1989 , vol. 9, # 10 p. 3482 - 3490 Title/Abstract Full Text Show Details

Titeler; Lyon; Glennon

Psychopharmacology, 1988 , vol. 94, # 2 p. 213 - 216 Title/Abstract Full Text Show Details

Gomez-Jeria; Cassels; Saavedra-Aguilar

European Journal of Medicinal Chemistry, 1987 , vol. 22, # 5 p. 433 - 437 Title/Abstract Full Text Show Details

Shannon; Battaglia; Glennon; Titeler

European journal of pharmacology, 1984 , vol. 102, # 1 p. 23 - 29 Title/Abstract Full Text Show Details

McGraw; Castagnoli Jr.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

3 of 4

4 of 4

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant human TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1

Results

no effect (related to human TAAR1)

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

receptor; activation of

Species or TestSystem (Pharmacological Data)

RD-HGA16 cells; genetically modified/infected with: recombinant rhesus monkey TAAR1

Further Details (Pharmacological Data)

TAAR1: trace amine-associated receptor 1

Results

no effect (related to monkey TAAR1)

Reference

Lewin, Anita H.; Miller, Gregory M.; Gilmour, Brian

Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 23 p. 7044 - 7048 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

serotonin binding affinity in the rat stomach fundus

Reference

Gomez-Jeria, Juan Sebastian; Cassels, Bruce K.; Saavedra-Aguilar, Juan Carlos

European Journal of Medicinal Chemistry, 1987 , vol. 22, p. 433 - 438 Title/Abstract Full Text View citing articles Show Details

Chemical Name: 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane Reaxys Registry Number: 2806354

CAS Registry Number: 15588-95-1 Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H19NO2

Molecular Weight: 209.288

InChI Key: NTJQREUGJKIARY-UHFFFAOYSA-N

8 prep out of 17 reactions.

Identification Physical Data (6) Spectra (3) Bioactivity (34)

Synthesize | Hide Details Find similar Chemical Names and Synonyms 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane, 1 (4 methyl 2,5 dimethoxyphenyl) 2 aminopropane, DOM, 2,5-dimethoxy-4methylamphetamine, 2,5-dimethoxy-4-methylphenylisopropylamine, 4-Methyl-2,5-dimethoxyamphetamine, [-]-2,5-dimethoxy-4-methylamphetamine Identification Substance Label (3) Label

Reference

DOM

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel

Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero

Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details

Serafine, Katherine M.; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2015 , vol. 355, # 3 p. 381 - 385

Title/Abstract Full Text View citing articles Show Details

10; DOM

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 8 p. 4661 - 4669 Title/Abstract Full Text View citing articles Show Details

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

Patent-Specific Data (2) Prophetic Compound

Related Markush Structure (RN)

prophetic product

11337200

Location in Patent

Reference Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.

Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text Show Details

Claim

Somerset Pharmaceuticals, Inc.

Patent: US6299901 B1, 2001 ; Title/Abstract Full Text Show Details

Somerset Pharmaceuticals, Inc.

Patent: US6319954 B1, 2001 ; Title/Abstract Full Text Show Details

Derivative (1) Derivative

Reference

DOM hydrochloride

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (1) Melting Point

Reference

60.5 - 61 °C

Dow Chemical Co.

Patent: GB1147739 , 1966 ; Chem.Abstr., 1969 , vol. 71, # 12781j Full Text Show Details

Chromatographic Data (1) Chromatographic data

Reference

CE (Capillar electrophoresis)

Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero

Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details

Further Information (3) Description (Further Information)

Reference

Further information

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Further information

Cornell; Fenselau

Archives of Mass Spectral Data, 1971 , vol. 2, p. 700 Full Text Show Details

Further information

Bellman

Journal - Association of Official Analytical Chemists, 1968 , vol. 51, p. 164,169 Full Text Show Details

Liquid/Liquid Systems (MCS) (1)

Description (Liquid/Liquid Systems (MCS))

Reference

Distribution between solvent 1 + 2

Barfknecht et al.

Journal of Medicinal Chemistry, 1975 , vol. 18, p. 208,209 Full Text Show Details

Spectra Mass Spectrometry (1) Reference Bellman

Journal - Association of Official Analytical Chemists, 1968 , vol. 51, p. 164,169 Full Text Show Details

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Cornell; Fenselau

Archives of Mass Spectral Data, 1971 , vol. 2, p. 700 Full Text Show Details

Fluorescence Spectroscopy (1) Description (Fluorescence Spectroscopy)

Reference

Fluorescence

Smythies et al.

Experientia, 1971 , vol. 27, p. 62,63 Full Text Show Details

Other Spectroscopic Methods (1) Description (Other Spectroscopic Methods)

Reference

Photoelectron spectrum

Domelsmith, L. N.; Eaton, Thomas A.; Houk, K. N.; Anderson, G. M.; Glennon, R. A.; et al.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 12 p. 1414 - 1421 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (32) 1 of 32

Comment (Pharmacological Data)

Bioactivities present

Reference

Coutts; Malicky

Canadian Journal of Chemistry, 1974 , vol. 52, # 3 p. 395 - 399 Title/Abstract Full Text View citing articles Show Details

Ho; Tansey; Balster; An; McIsaac; Harris

Journal of medicinal chemistry, 1970 , vol. 13, # 1 p. 134 - 135 Title/Abstract Full Text View citing articles Show Details

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Jacob III; Anderson III; Meshul; Shulgin; Castagnoli Jr.

Journal of Medicinal Chemistry, 1977 , vol. 20, # 10 p. 1235 - 1239 Title/Abstract Full Text View citing articles Show Details

Glennon; Liebowitz; Mack

Journal of Medicinal Chemistry, 1978 , vol. 21, # 8 p. 822 - 825 Title/Abstract Full Text View citing articles Show Details

Somerset Pharmaceuticals, Inc.

Patent: US6299901 B1, 2001 ; Title/Abstract Full Text Show Details

Somerset Pharmaceuticals, Inc.

Patent: US6319954 B1, 2001 ; Title/Abstract Full Text Show Details

Caron, Marc G.; Sotnikova, Tatyana D.; Gainetdinov, Raul R.

Patent: US2007/27208 A1, 2007 ; Title/Abstract Full Text Show Details

BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY

Patent: WO2006/113557 A3, 2006 ;

Title/Abstract Full Text Show Details

Bellman

Journal - Association of Official Analytical Chemists, 1968 , vol. 51, p. 164,169 Full Text Show Details

Ho et al.

Journal of Medicinal Chemistry, 1971 , vol. 14, p. 1132 Full Text View citing articles Show Details

Barfknecht et al.

Journal of Medicinal Chemistry, 1975 , vol. 18, p. 208,209 Full Text Show Details

Ho; Tansey

Journal of medicinal chemistry, 1971 , vol. 14, # 2 p. 156 - 157 Title/Abstract Full Text View citing articles Show Details

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Cornell; Fenselau

Archives of Mass Spectral Data, 1971 , vol. 2, p. 700 Full Text Show Details

Ho; Estevez; Tansey; Englert; Creaven; McIsaac

Journal of medicinal chemistry, 1971 , vol. 14, # 2 p. 158 - 160 Title/Abstract Full Text View citing articles Show Details

Dow Chemical Co.

Patent: GB1147739 , 1966 ; Chem.Abstr., 1969 , vol. 71, # 12781j Full Text Show Details

Smythies et al.

Experientia, 1971 , vol. 27, p. 62,63 Full Text Show Details

Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon

Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1032 - 1036 Title/Abstract Full Text View citing articles Show Details

2 of 32

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Snyder; Oberlender; Johnson; Huang

Journal of Medicinal Chemistry, 1991 , vol. 34, # 1 p. 276 - 281 Title/Abstract Full Text View citing articles Show Details

Johnson; Frescas; Oberlender; Nichols

Journal of Medicinal Chemistry, 1991 , vol. 34, # 5 p. 1662 - 1668 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 Title/Abstract Full Text View citing articles Show Details

McGraw, N. Peter; Castagnoli, N.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

Domelsmith, L. N.; Eaton, Thomas A.; Houk, K. N.; Anderson, G. M.; Glennon, R. A.; et al.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 12 p. 1414 - 1421 Title/Abstract Full Text View citing articles Show Details

Glennon; Liebowitz; Anderson III

Journal of Medicinal Chemistry, 1980 , vol. 23, # 3 p. 294 - 299 Title/Abstract Full Text View citing articles Show Details

Oberlender, Robert A.; Kothari, Paresh J.; Nichols, David E.; Zabik, Joseph E.

Journal of Medicinal Chemistry, 1984 , vol. 27, # 6 p. 788 - 792 Title/Abstract Full Text View citing articles Show Details

Lyon; Titeler; McKenney; Magee; Glennon

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 630 - 634 Title/Abstract Full Text View citing articles Show Details

Glennon; Jacyno; Young; McKenney; Nelson

Journal of Medicinal Chemistry, 1984 , vol. 27, # 1 p. 41 - 45 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text View citing articles Show Details

Glennon; Young; Benington; Morin

Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details

Glennon; Titeler; Lyon; Slusher

Journal of Medicinal Chemistry, 1988 , vol. 31, # 4 p. 867 - 870 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; Slusher, R. M.; Lyon, Robert A.; Titeler, Milt; McKenney, J. D.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2375 - 2380 Title/Abstract Full Text View citing articles Show Details

Oberlender; Ramachandran; Johnson; Huang; Nichols

Journal of Medicinal Chemistry, 1995 , vol. 38, # 18 p. 3593 - 3601 Title/Abstract Full Text View citing articles Show Details

Solbach, M.; Guendisch, D.; Wuellner, U.; Blocher, A.; Kovar, K.-A.; Machulla, H.-J.

Journal of Labelled Compounds and Radiopharmaceuticals, 1997 , vol. 40, p. 522 - 524 Title/Abstract Full Text Show Details

Clare, Brian W.

Journal of Medicinal Chemistry, 1998 , vol. 41, # 20 p. 3845 - 3856 Title/Abstract Full Text View citing articles Show Details

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo

British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

Altun, Ahmet; Golcuk, Kurtulus; Kumru, Mustafa; Jalbout, Abraham F.

Bioorganic and Medicinal Chemistry, 2003 , vol. 11, # 18 p. 3861 - 3868 Title/Abstract Full Text View citing articles Show Details

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel

Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details

3 of 32

Comment (Pharmacological Data)

Bioactivities present

Reference

Thakur, Mamta; Thakur, Abhilash; Khadikar, Padmakar V.

Bioorganic and Medicinal Chemistry, 2004 , vol. 12, # 4 p. 825 - 831 Title/Abstract Full Text View citing articles Show Details

Gallardo-Godoy, Alejandra; Fierro, Angelica; McLean, Thomas H.; Castillo, Mariano; Cassels, Bruce K.; Reyes-Parada, Miguel; Nichols, David E.

Journal of Medicinal Chemistry, 2005 , vol. 48, # 7 p. 2407 - 2419 Title/Abstract Full Text View citing articles Show Details

Roth; Shoham; Choudhary; Khan

Molecular Pharmacology, 1997 , vol. 52, # 2 p. 259 - 266 Title/Abstract Full Text View citing articles Show Details

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Fantegrossi, William E.; Murnane, Kevin S.; Reissig, Chad J.

Biochemical Pharmacology, 2008 , vol. 75, # 1 p. 17 - 33 Title/Abstract Full Text View citing articles Show Details

Li, Jun-Xu; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2008 , vol. 324, # 2 p. 827 - 833 Title/Abstract Full Text View citing articles Show Details

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 8 p. 4661 - 4669 Title/Abstract Full Text View citing articles Show Details

MOUNT SINAI SCHOOL OF MEDICINE OF NEW YORK UNIVERSITY

Patent: WO2009/100384 A2, 2009 ; Title/Abstract Full Text Show Details

Blaazer, Antoni R.; Smid, Pieter; Kruse, Chris G.

ChemMedChem, 2008 , vol. 3, # 9 p. 1299 - 1309 Title/Abstract Full Text View citing articles Show Details

Barfknecht; Nichols; Dunn III

Journal of Medicinal Chemistry, 1975 , vol. 18, # 2 p. 208 - 210 Title/Abstract Full Text Show Details

Aldous; Barrass; Brewster; Buxton; Green; Pinder; Rich; Skeels; Tutt

Journal of Medicinal Chemistry, 1974 , vol. 17, # 10 p. 1100 - 1111 Title/Abstract Full Text Show Details

Standridge; Howell; Gylys; Partyka; Shulgin

Journal of medicinal chemistry, 1976 , vol. 19, # 12 p. 1400 - 1404 Title/Abstract Full Text Show Details

Lopatka; Brewerton; Brooks; Cook; Paton

Research Communications in Chemical Pathology and Pharmacology, 1976 , vol. 14, # 4 p. 677 - 687 Title/Abstract Full Text View citing articles Show Details

Kier; Hall

Journal of Medicinal Chemistry, 1977 , vol. 20, # 12 p. 1631 - 1636 Title/Abstract Full Text Show Details

Leysen

Current drug targets. CNS and neurological disorders, 2004 , vol. 3, # 1 p. 11 - 26 Title/Abstract Full Text Show Details

Chambers, James J; Kurrasch-Orbaugh, Deborah M; Nichols, David E

Bioorganic and medicinal chemistry letters, 2002 , vol. 12, # 15 p. 1997 - 1999 Title/Abstract Full Text Show Details

Roth, Bryan L.; Choudhary; Khan; Uluer

Journal of Pharmacology and Experimental Therapeutics, 1997 , vol. 280, # 2 p. 576 - 583 Title/Abstract Full Text View citing articles Show Details

Pauwels; Van Gompel; Leysen

Biochemical Pharmacology, 1993 , vol. 45, # 2 p. 375 - 383 Title/Abstract Full Text Show Details

Leonhardt; Gorospe; Hoffman; Teitler

Molecular Pharmacology, 1992 , vol. 42, # 2 p. 328 - 335 Title/Abstract Full Text Show Details

Glennon; Raghupathi; Bartyzel; Teitler; Leonhardt

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

Bioactivities present

Reference

Oberlender; Nichols

Journal of Pharmacology and Experimental Therapeutics, 1990 , vol. 255, # 3 p. 1098 - 1106 Title/Abstract Full Text View citing articles Show Details

Clare

Journal of Medicinal Chemistry, 1990 , vol. 33, # 2 p. 687 - 702 Title/Abstract Full Text Show Details

McKenna; Peroutka

The Journal of neuroscience : the official journal of the Society for Neuroscience, 1989 , vol. 9, # 10 p. 3482 - 3490 Title/Abstract Full Text Show Details

Titeler; Lyon; Glennon

Psychopharmacology, 1988 , vol. 94, # 2 p. 213 - 216 Title/Abstract Full Text Show Details

Oberlender; Nichols

Psychopharmacology, 1988 , vol. 95, # 1 p. 71 - 76 Title/Abstract Full Text Show Details

Glennon

Journal of Medicinal Chemistry, 1987 , vol. 30, # 1 p. 1 - 12 Title/Abstract Full Text Show Details

Rasmussen; Glennon; Aghajanian

European Journal of Pharmacology, 1986 , vol. 132, # 1 p. 79 - 82 Title/Abstract Full Text Show Details

Glennon; Slusher; Lyon; Titeler; McKenney

Journal of medicinal chemistry, 1986 , vol. 29, # 11 p. 2375 - 2380 Title/Abstract Full Text Show Details

Nichols; Hoffman; Oberlender; Riggs

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 302 - 304 Title/Abstract Full Text Show Details

Glennon; McKenney; Lyon; Titeler

Journal of medicinal chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text Show Details

Oberlender; Kothari; Nichols; Zabik

Journal of Medicinal Chemistry, 1984 , vol. 27, # 6 p. 788 - 792 Title/Abstract Full Text View citing articles Show Details

Shannon; Battaglia; Glennon; Titeler

European journal of pharmacology, 1984 , vol. 102, # 1 p. 23 - 29 Title/Abstract Full Text Show Details

Domelsmith; Eaton; Houk; Anderson III; Glennon; Shulgin; Castagnoli Jr.; Kollman

Journal of Medicinal Chemistry, 1981 , vol. 24, # 12 p. 1414 - 1421 Title/Abstract Full Text Show Details

Burrai, Lucia; Nieddu, Maria; Pirisi, Maria Antonietta; Carta, Antonio; Briguglio, Irene; Boatto, Gianpiero

Chirality, 2013 , vol. 25, # 10 p. 617 - 621 Title/Abstract Full Text View citing articles Show Details

McGraw; Castagnoli Jr.

Journal of Medicinal Chemistry, 1981 , vol. 24, # 3 p. 299 - 304 Title/Abstract Full Text View citing articles Show Details

Leonard

British journal of pharmacology, 1972 , vol. 45, # 1 p. 165P-166P Title/Abstract Full Text View citing articles Show Details

1972 , p. 340 Full Text Show Details

Raj K. Razdan

Annual reports in medicinal chemistry, 1969 , vol. 5, p. 23 - 29 Title/Abstract Full Text Show Details

M.A. Davis Annual reports in medicinal chemistry, 1968 , vol. 4, p. 13 - 27 Title/Abstract Full Text Show Details M. A. Davis Annual reports in medicinal chemistry, 1967 , vol. 3, p. 14 - 27 Title/Abstract Full Text Show Details 5 of 32

Comment (Pharmacological Data)

Bioactivities present

Reference

S.P.Gupta

Chemical reviews, 1989 , vol. 89, # 8 p. 1765 - 1800 Title/Abstract Full Text Show Details

SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL

Chemical reviews, 1983 , vol. 83, # 6 p. 633 - 649 Title/Abstract Full Text Show Details

http://www.unodc.org/unodc/en/data-and-analysis/bulletin/bulletin_1970-01-01_1_page006.html Full Text Show Details

http://www2.siri.org/msds/tox/f/q88/q368.html Full Text Show Details

Psychotropic Drugs and Related Compounds, 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972, 340, 1972 , p. 340 Full Text Show Details

Eshleman, Amy J.; Forster, Michael J.; Wolfrum, Katherine M.; Johnson, Robert A.; Janowsky, Aaron; Gatch, Michael B.

Psychopharmacology, 2014 , vol. 231, # 5 p. 875 - 888 Title/Abstract Full Text View citing articles Show Details

Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan

Patent: EP2950104 A1, 2015 ; Title/Abstract Full Text Show Details

Serafine, Katherine M.; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2015 , vol. 355, # 3 p. 381 - 385 Title/Abstract Full Text View citing articles Show Details

Rojek, Sebastian; Bolechała, Filip; Kula, Karol; Maciów-Głąb, Martyna; Kłys, Małgorzata

Legal Medicine, 2016 , vol. 21, p. 64 - 72 Title/Abstract Full Text View citing articles Show Details

Goodwin, Amy K.

Journal of Pharmacological and Toxicological Methods, 2016 , vol. 82, p. 31 - 36 Title/Abstract Full Text View citing articles Show Details

Garcia-Romeu, Albert; Kersgaard, Brennan; Addy, Peter H.

Experimental and Clinical Psychopharmacology, 2016 , vol. 24, # 4 p. 229 - 268 Title/Abstract Full Text View citing articles Show Details

Glicksberg, Lindsay; Bryand, Kelsie; Kerrigan, Sarah

Journal of Chromatography B: Analytical Technologies in the Biomedical and Life Sciences, 2016 , vol. 1035, p. 91 - 103 Title/Abstract Full Text Show Details

Carbonaro, Theresa M.; Gatch, Michael B.

Brain Research Bulletin, 2016 , vol. 126, p. 74 - 88 Title/Abstract Full Text Show Details

Li, Rongtao; Morris-Natschke, Susan L.; Lee, Kuo-Hsiung

Natural Product Reports, 2016 , vol. 33, # 10 p. 1166 - 1226 Title/Abstract Full Text Show Details

Saz; Marina

Journal of Chromatography A, 2016 , vol. 1467, p. 79 - 94 Title/Abstract Full Text Show Details

Kyzar, Evan J.; Kalueff, Allan V.

Zebrafish, 2016 , vol. 13, # 5 p. 379 - 390 Title/Abstract Full Text Show Details

Drinkenburg, Wilhelmus H.I.M.; Ruigt, Gé S.F.; Ahnaou, Abdallah

Neuropsychobiology, 2016 , vol. 72, # 3-4 p. 151 - 164 Title/Abstract Full Text Show Details

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Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Randox Laboratories Ltd.; Benchik, Elouard; Fitzgerald, Peter; Lowry, Philip; McConnell, Ivan

Patent: EP2950104 A1, 2015 ; Title/Abstract Full Text Show Details

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9 of 32

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Serafine, Katherine M.; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2015 , vol. 355, # 3 p. 381 - 385 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

physiological behaviour discussed

Reference

Eshleman, Amy J.; Forster, Michael J.; Wolfrum, Katherine M.; Johnson, Robert A.; Janowsky, Aaron; Gatch, Michael B.

Psychopharmacology, 2014 , vol. 231, # 5 p. 875 - 888 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

rhesus monkey

Sex

male and female

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.32 mg/kg

Kind of Dosing (Pharmacological Data)

vehicle: saline

Method (Pharmacological Data)

monkeys were trained to discriminate between title comp. and saline in two-lever paradigm under fixed ratio 5 schedule of stimulus-shock termination; injections were made 30 min before 10-min response periods

Further Details (Pharmacological Data)

number of sessions required for stable discrimination was recorded

Results

monkeys learned to discriminate between title comp. and saline after an average of 116 (range, 85 - 166) sessions

Reference

Li, Jun-Xu; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2008 , vol. 324, # 2 p. 827 - 833

Title/Abstract Full Text View citing articles Show Details

10 of 32

11 of 32

12 of 32

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

rhesus monkey

Sex

male and female

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.032 - 0.32 mg/kg

Kind of Dosing (Pharmacological Data)

vehicle: saline

Method (Pharmacological Data)

training to discriminate between 0.32 mg/kg title comp. and saline in 2-lever paradigm under fixed ratio 5 schedule of stimulus-shock termination; injections made 30 min before 10-min response periods; testing performed after discrimination was stable

Further Details (Pharmacological Data)

control: vehicle; reference comp. (ED50, mg/kg): (+)lysergic acid diethylamide (LSD, 0.008), (-)-1-(2,5-dimethoxy-4-methylphenyl)-2aminopropane ((-)DOM, 0.1), 2C-T-7 (0.113), quipazine (1.59), salvinorin A, U504188, amphetamine, cocaine, and other

Type (Pharmacological Data)

ED50

Value of Type (Pharmacological Data)

0.124 mg/kg

Results

title comp. dose-dependently increased responding on title comp.-associated lever; LSD, (-)DOM, 2C-T-7, or quipazine could substitute for title comp. and ketamine or phencyclidine partially mimicked it, while other tested compounds did not; table

Reference

Li, Jun-Xu; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2008 , vol. 324, # 2 p. 827 - 833 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

rhesus monkey

Sex

male and female

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.32 mg/kg

Kind of Dosing (Pharmacological Data)

vehicle: saline

Method (Pharmacological Data)

monkeys trained to discriminate between 0.32 mg/kg title comp. and saline in two-lever paradigm under FR5 schedule of stimulus-shock termination; injections made 30 min before 10-min response periods; testing performed after discrimination was stable

Further Details (Pharmacological Data)

control: vehicle; further investigations using pretreatment with 5-hydroxytryptamine (5-HT) receptor antagonists MDL100907, MDL100009, ketanserin, or ritanserin and dopamine receptor antagonist haloperidol; FR: fixed ratio

Results

title comp. increased responding on title comp.-associated lever; effect was mediated by 5-HT receptor, but not by dopamine receptor; fig.

Reference

Li, Jun-Xu; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2008 , vol. 324, # 2 p. 827 - 833 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological

rhesus monkey

Data)

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Sex

male and female

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.032 - 0.32 mg/kg

Kind of Dosing (Pharmacological Data)

vehicle: saline

Method (Pharmacological Data)

Further Details (Pharmacological Data)

response rate was recorded for 10 min starting 15 - 240 min after title comp. administration; control: vehicle; FR: fixed ratio

Results

0.1 - 0.32 mg/kg title comp. reduced average response rate; effect was maximal at 15 min postdose and gradually declined to near control level at 240 min postdose; 30 min after 0.32 mg/kg title comp. injection response rate was 52percent of control; fig.

Reference

Li, Jun-Xu; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2008 , vol. 324, # 2 p. 827 - 833 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

Species or TestSystem (Pharmacological Data)

rhesus monkey

Sex

male and female

Route of Application

subcutaneous

Concentration (Pharmacological Data)

0.32 mg/kg

Kind of Dosing (Pharmacological Data)

vehicle: saline

Method (Pharmacological Data)

monkeys trained to discriminate between title comp. and saline in two-lever paradigm under fixed ratio 5 schedule of stimulus-shock termination; injections made 30 min before 10-min response periods; testing performed after discrimination was stable

Further Details (Pharmacological Data)

responding on title comp.-associated lever was recorded for 10 min starting 15 - 240 min after title comp. administration; control: vehicle

Results

title comp. increased responding on title comp.-associated lever; discriminative stimulus effect was evident 15 min and maximal 30 min postdose; at 60 and 240 min postdose 81percent and 13percent responding was on title comp.-associated lever, resp.; fig.

Reference

Li, Jun-Xu; Rice, Kenner C.; France, Charles P.

Journal of Pharmacology and Experimental Therapeutics, 2008 , vol. 324, # 2 p. 827 - 833 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

functional activity

Species or TestSystem (Pharmacological Data)

rat

Method (Pharmacological Data)

drug discrimination assay using rats trained to distinguish the 5-HT2A receptor agonist LSD from saline; rat behavior observed

Results

title comp. indirectly determined to be an agonist of 5-HT2A receptor

Reference

Parker, Matthew A.; Kurrasch, Deborah M.; Nichols, David E.

Bioorganic and Medicinal Chemistry, 2008 , vol. 16, # 8 p. 4661 - 4669 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

behavioural symptoms

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Species or TestSystem (Pharmacological Data)

Sprague-Dawley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

8.4 μmol/kg

Method (Pharmacological Data)

immediately after title comp. injection rats placed in dark Plexiglas box and number of head shakes was quantified for 25 min, starting 5 min after title comp. administration

Further Details (Pharmacological Data)

control: saline; 5-HT: serotonin

Results

title comp. induced robust head shake behavior in comparison with control (figure)

Reference

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

CHO-1C19 cells expressing human 5-HT2A receptors

Method (Pharmacological Data)

cells in serum-free medium labeled with 1 μCi/ml myo-<3H>inositol 24 h and with 0.1 μCi/ml <3H>AA 4 h at 37 deg C; then treated 10 min with title comp.; dose-response curve for total IP accumulation and AA release calculated

Further Details (Pharmacological Data)

control: vehicle; AA: arachidonic acid; IP: inositol phosphate; CHO: Chinese hamster ovary; data expressed as percent of maximal response to 5HT; 5-HT: serotonin; PLA2 and PLC: phospholipase A2 and phospholipase C, resp.; RE: relative efficacy

Results

title comp. had similar relative efficacies for PLC-mediated IP accumulation (RE = ca. 40percent and pEC50 = 5.83) and for PLA2-mediated AA release (RE = ca. 45percent, pEC50 = 5.77) (figures, table)

Reference

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

agonist

Species or TestSystem (Pharmacological Data)

CHO-1C19 cells expressing human 5-HT2C receptors

Concentration (Pharmacological Data)

1E-09 - 5E-05 mol/l

Method (Pharmacological Data)

Further Details (Pharmacological Data)

Results

title comp. preferentially stimulated PLA2-mediated AA release (RE = ca. 120percent, pEC50 = 6.08); RE for PLC-mediated IP accumulation was ca. 85percent, pEC50 = 5.79 (figures, table)

Reference

Moya, Pablo R.; Berg, Kelly A.; Gutierrez-Hernandez, Manuel A.; Saez-Briones, Patricio; Reyes-Parada, Miguel; Cassels, Bruce K.; Clarke, William P.

Journal of Pharmacology and Experimental Therapeutics, 2007 , vol. 321, # 3 p. 1054 - 1061 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; inhib. of

Species or Test-

IIBCE rat brain mitochondrial monoamine oxidase B

System (Pharmacological Data)

19 of 32

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22 of 32

Sex

male

Concentration (Pharmacological Data)

0.01 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

in distilled water

Method (Pharmacological Data)

MAO-B activity determined by HPLC with electrochemical detection after incubation with selective substrate of DMAPEA in presence of title comp. at 37 deg C for 5 min, pH 7.4; DMAPEA and its MAO-B metabolite DMAPAA used to calculate MAO-B activity

Further Details (Pharmacological Data)

MAO-B = monoamine oxidase B; DMAPEA = 4-dimethylaminophenethylamine, 5 μmol/l; DMAPAA = 4-dimethylaminophenylacetic acid

Comment (Pharmacological Data)

No effect

Reference

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel

Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details

Effect (Pharmacological Data)

enzyme; inhib. of

Species or TestSystem (Pharmacological Data)

IIBCE rat brain mitochondrial monoamine oxidase A

Sex

male

Concentration (Pharmacological Data)

0.01 - 100 μmol/l

Kind of Dosing (Pharmacological Data)

in distilled water

Method (Pharmacological Data)

MAO-A activity determined by HPLC with electrochemical detection after incubation with selective substrate of 5-HT in presence of title comp. at 37 deg C for 10 min, pH 7.4; 5-HT and its MAO-A metabolite 5-HIAA used to calculate MAO-A activity

Further Details (Pharmacological Data)

MAO-A = monoamine oxidase A; 5-HT = serotonin, 2.5 μmol/l; 5-HIAA = 5-hydroxyindoleacetic acid

Type (Pharmacological Data)

IC50

Value of Type (Pharmacological Data)

24 μmol/l

Reference

Scorza, Ma. Cecilia; Carrau, Cecilia; Silveira, Rodolfo; Zapata-Torres, Gerald; Cassels, Bruce K.; Reyes-Parada, Miguel

Biochemical Pharmacology, 1997 , vol. 54, # 12 p. 1361 - 1369 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

in vivo hallucinogenic effect in LSD-trained rats ED50=0.61 μmol/kg (ip); in vitro binding at 5-HT2 serotonin receptor in rat frontal cortex

Reference

Oberlender; Ramachandran; Johnson; Huang; Nichols

Journal of Medicinal Chemistry, 1995 , vol. 38, # 18 p. 3593 - 3601 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

uptake inhibition of synaptosomal <3H>-5-HT: IC50 = 10655 nM

Reference

Johnson; Frescas; Oberlender; Nichols

Journal of Medicinal Chemistry, 1991 , vol. 34, # 5 p. 1662 - 1668 Title/Abstract Full Text View citing articles Show Details

ability to displace<125I>-(R)-DOI (<125I>-(R)-1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane) from rat cortical homogenate 5-HT receptors

Comment (Pharmacological Data)

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Reference

Nichols; Snyder; Oberlender; Johnson; Huang

Journal of Medicinal Chemistry, 1991 , vol. 34, # 1 p. 276 - 281 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

activity in the two-lever drug-discrimination paradigm in rats trained to discriminate saline from LSD tartrate (0.08 mg/kg); ED50= 0.89 μmol/kg

Reference

Nichols; Snyder; Oberlender; Johnson; Huang

Journal of Medicinal Chemistry, 1991 , vol. 34, # 1 p. 276 - 281 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

5-HT2 serotonin antagonist activity

Reference

Seggel; Yousif; Lyon; Titeler; Roth; Suba; Glennon

Journal of Medicinal Chemistry, 1990 , vol. 33, # 3 p. 1032 - 1036 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

Serotonergic agonist of central serotonin (5-HT) binding sites.

Reference

Glennon; Titeler; Lyon; Slusher

Journal of Medicinal Chemistry, 1988 , vol. 31, # 4 p. 867 - 870 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

stimulus generalization in rats trained to discriminate 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) from saline (ED50 = 0.44 mg/kg)

Reference

Lyon; Titeler; McKenney; Magee; Glennon

Journal of Medicinal Chemistry, 1986 , vol. 29, # 5 p. 630 - 634 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

in vivo (male Sprague-Dawley rats) stimulus antagonism test (discrimination studies using rats trained to discriminate a 5-HT1 or 5-HT2 agonist from saline)

Reference

Glennon, Richard A.; Slusher, R. M.; Lyon, Robert A.; Titeler, Milt; McKenney, J. D.

Journal of Medicinal Chemistry, 1986 , vol. 29, # 11 p. 2375 - 2380 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

stimulus generalization studies on rats ED50 = 0.99 mg/kg t

Reference

Glennon, Richard A.; McKenney, J. D.; Lyon, Robert A.; Titeler, Milt

Journal of Medicinal Chemistry, 1986 , vol. 29, # 2 p. 194 - 199 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

drug discrimination paradigm (LSD as the training drug stimulus): ED50 = 0.148 mg/kg (rats)

Reference

Oberlender, Robert A.; Kothari, Paresh J.; Nichols, David E.; Zabik, Joseph E.

Journal of Medicinal Chemistry, 1984 , vol. 27, # 6 p. 788 - 792 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

the serotonin (5HT) receptor affinities, human hallucinogen

Reference

Glennon; Young; Benington; Morin

Journal of Medicinal Chemistry, 1982 , vol. 25, # 10 p. 1163 - 1168 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

Forts.: Mengen von 1-<2,5-Dimethoxy-4-methyl-phenyl-aceton> (4) ausgeschieden.

Reference

Ho; Estevez; Tansey; Englert; Creaven; McIsaac

Journal of medicinal chemistry, 1971 , vol. 14, # 2 p. 158 - 160 Title/Abstract Full Text View citing articles Show Details

Comment

Bach Verabreichung des Hydrochlorids an Ratten( 'ip' in Salzloesung) werden im Urin und Faeces (+-)-2-Amino-1-<4-hydroxymethyl-2,5-

(Pharmacological Data)

dimethoxy-phenyl>-propan (2) und (+-)-4-<2-Amino-propyl>-2,5-dimethoxy-benzoesaeure(3) sowie kleine ...

Reference

Ho; Estevez; Tansey; Englert; Creaven; McIsaac

Journal of medicinal chemistry, 1971 , vol. 14, # 2 p. 158 - 160 Title/Abstract Full Text View citing articles Show Details

Ecotoxicology (2) 1 of 2

Effect (Ecotoxicology)

membrane current; induction of

Species or TestSystem (Ecotoxicology)

Xenopus laevis oocyte

Kind of Dosing (Ecotoxicology)

used as hydrochloride; 6 - 7 concentrations were applied

Method (Ecotoxicology)

oocytes expressing rat 5-HT2A receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; addition of increasing concentrations of title comp. for 10 s; stimulation of membrane currents was determined

Further Details (Ecotoxicology)

2 of 2

5-HT: serotonin; Imax: maximal current relative to that evoked by 5-HT

Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

29 nmol/l

Results

title comp. concentration-dependently induced membrane current with Imax = 44 percent (table)

Reference

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo

British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details

Effect (Ecotoxicology)

membrane current; induction of

Species or TestSystem (Ecotoxicology)

Xenopus laevis oocyte

Kind of Dosing (Ecotoxicology)

used as hydrochloride; 6 - 7 concentrations were applied

Method (Ecotoxicology)

oocytes expressing rat 5-HT2C receptors; two-electrode voltage clamp at -70 mV; standard medium at 15 deg C; addition of increasing concentrations of title comp. for 10 s; stimulation of membrane currents was determined

Further Details (Ecotoxicology)

5-HT: serotonin; Imax: maximal current relative to that evoked by 5-HT

Type (Ecotoxicology)

EC50

Value of Type (Ecotoxicology)

423 nmol/l

Results

title comp. concentration-dependently induced membrane current with Imax = 81 percent (table)

Reference

Acuna-Castillo, Claudio; Villalobos, Claudio; Moya, Pablo R; Saez, Patricio; Cassels, Bruce K; Huidobro-Toro, J Pablo

British journal of pharmacology, 2002 , vol. 136, # 4 p. 510 - 519 Title/Abstract Full Text View citing articles Show Details

Reaxys Registry Number: 4905867

CAS Registry Number: 15588-95-1, 26011-50-7, 43061-13-8, 43061-14-9 Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H19NO2

Molecular Weight: 209.288

InChI Key: NTJQREUGJKIARY-UHFFFAOYSA-N

Synthesize | Hide Details Find similar

no reactions.

Identification Bioactivity (2)

Identification Substance Label (1) Label

Reference

1-(-)

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (2) 1 of 2

2 of 2

Comment (Pharmacological Data)

Bioactivities present

Reference

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

binding affinity at 5-HT1C and 5-HT2 serotonin receptors; lack of selectivity

Reference

Glennon, Richard A.; Raghupathi, Reva; Bartyzel, Piotr; Teitler, Milt; Leonhardt, Sigrun

Journal of Medicinal Chemistry, 1992 , vol. 35, # 4 p. 734 - 740 Title/Abstract Full Text View citing articles Show Details

Reaxys Registry Number: 2738217

CAS Registry Number: 61471-46-3 Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H17D2NO2

Molecular Weight: 211.272

InChI Key: NTJQREUGJKIARY-JYFDYMOTSA-N

no reactions.

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Identification Substance Label (1) Label

Reference

1-d2, R%4&=R%2&=R%5&=CH

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Physical Data Further Information (1) Description (Further Information)

Reference

Further information

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Spectra Mass Spectrometry (1) Reference

Identification Physical Data (1) Spectra (1) Bioactivity (1)

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

J.S.; Castagnoli Jr. Journal of Medicinal Chemistry, 1977 , vol. 20, # 3 p. 414 - 421 Title/Abstract Full Text Show Details Reaxys Registry Number: 2981587

CAS Registry Number: 61471-46-3 Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H17D2NO2

Molecular Weight: 211.272

InChI Key: NTJQREUGJKIARY-JYFDYMOTSA-N

1 prep out of 1 reactions.

Identification Spectra (1)

Identification

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Identification Substance Label (1) Label

Reference

1-d2

Mc Graw et al.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 185,188 Full Text Show Details

Derivative (1) Comment (Derivative)

Reference

Hydrochlorid: F:185-188grad

Mc Graw et al.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 185,188 Full Text Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Reference

NMR

Mc Graw et al.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 185,188 Full Text Show Details

Reaxys Registry Number: 2984922

Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H16D3NO2

Molecular Weight: 212.265

InChI Key: NTJQREUGJKIARY-FIBGUPNXSA-N

8 prep out of 8 reactions.

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Identification Substance Label (1) Label

Reference

1-d3

Zweig,J.S.; Castagnoli,N.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 414 - 421 Full Text View citing articles Show Details

Reaxys Registry Number: 2855113

Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H17T2NO2

Molecular Weight: 213.272

InChI Key: NTJQREUGJKIARY-VPHBPMBWSA-N

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Identification Substance Label (1) Label

Reference

Jacob III et al.

Journal of Medicinal Chemistry, 1979 , vol. 22, p. 662,668 Full Text Show Details

Derivative (1) Comment (Derivative)

Reference

Hydrochlorid: F=185-186grad

Jacob III et al.

Journal of Medicinal Chemistry, 1979 , vol. 22, p. 662,668 Full Text Show Details

Physical Data Melting Point (1) Melting Point

Reference

58 - 60 °C

Jacob III et al.

Journal of Medicinal Chemistry, 1979 , vol. 22, p. 662,668

1 prep out of 1 reactions.

Identification Physical Data (1)

Full Text Show Details

Chemical Name: (+/-)-2-(2,5-[2H6]dimethoxy-4-methylphenyl)-1-methylethylamine Reaxys Registry Number: 2755172

CAS Registry Number: 60124-87-0 Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H9NO2H4(2)H6

5 prep out of 5 reactions.

Molecular Weight: 215.241

InChI Key: NTJQREUGJKIARY-LIJFRPJRSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+/-)-2-(2,5-[2H6]dimethoxy-4-methylphenyl)-1-methylethylamine Identification Substance Label (3) Label

Reference

Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao

Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 7 p. 660 - 665 Title/Abstract Full Text View citing articles Show Details

1-d6, R%4&=CH3, R%2&=R%5</su

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Fentiman; Foltz

Journal of Labelled Compounds and Radiopharmaceuticals, 1976 , vol. 12, p. 69,74 Full Text Show Details

Derivative (1) Comment (Derivative)

Reference

Hydrochlorid: NMR; B.: Nitropropen 15-d6, LiAlH4 --> 1-d6

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Physical Data Melting Point (2) Melting Point

Reference

200 - 201 °C

Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao

Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 7 p. 660 - 665 Title/Abstract Full Text View citing articles Show Details

186 - 188 °C

Fentiman; Foltz

Journal of Labelled Compounds and Radiopharmaceuticals, 1976 , vol. 12, p. 69,74 Full Text Show Details

Boiling Point (1) Boiling Point

Pressure (Boiling Point)

Reference

85 - 105 °C

0.3 Torr

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Identification Physical Data (3) Spectra (5)

Spectra NMR Spectroscopy (2) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Chemical shifts

13C

CDCl3

75.5 MHz

Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao

Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 7 p. 660 - 665 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

CDCl3

300 MHz

Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao

Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 7 p. 660 - 665 Title/Abstract Full Text View citing articles Show Details

Reference

IR Spectroscopy (1) Description (IR Spectroscopy)

Solvent (IR Spectroscopy)

Reference

Bands

KBr

Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao

Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 7 p. 660 - 665 Title/Abstract Full Text View citing articles Show Details

Mass Spectrometry (2) Description (Mass Spectrometry)

Reference

spectrum electron impact (EI)

Shaikh, Ajam C.; Wang, Yu-Yun; Chen, Chinpiao

Journal of Labelled Compounds and Radiopharmaceuticals, 2007 , vol. 50, # 7 p. 660 - 665 Title/Abstract Full Text View citing articles Show Details

Weinkam et al.

Analytical Chemistry, 1976 , vol. 48, p. 203,204 Full Text Show Details

Reaxys Registry Number: 2870718

CAS Registry Number: 70097-37-9 Type of Substance: isocyclic Molecular Formula: C12H19NO2

Linear Structure Formula: C12H14T5NO2

Molecular Weight: 219.249

InChI Key: NTJQREUGJKIARY-JDWBOORZSA-N 10

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Identification Substance Label (1) Label

Reference

Jacob III et al.

Journal of Medicinal Chemistry, 1979 , vol. 22, p. 662,668 Full Text Show Details

Physical Data Melting Point (1) Melting Point

Reference

187 - 188 °C

Jacob III et al.

Journal of Medicinal Chemistry, 1979 , vol. 22, p. 662,668

1 prep out of 1 reactions.

Identification Physical Data (1)

Full Text Show Details

Chemical Name: DOM hydrochloride

no reactions.

Reaxys Registry Number: 5314056

CAS Registry Number: 15589-00-1 Type of Substance: isocyclic Molecular Formula: C12H19NO2*ClH Linear Structure Formula: C12H19NO2*ClH Molecular Weight: 245.749

InChI Key: IPIMRNFGYPQKAM-UHFFFAOYSA-N

Identification Physical Data (5) Spectra (7) Bioactivity (3)

Synthesize | Hide Details Find similar Chemical Names and Synonyms DOM hydrochloride, (+/-)-1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane hydrochloride, 2,5-dimethoxy-4-methylamphetamine hydrochloride, (dl)-2,5-dimethoxy-4-methylamphetamine HCl, 1-(2,5-dimethoxy-4-methylphenyl)-2-aminopropane (DOM) Identification Substance Label (8) Label

Reference

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

DOM

Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.

Medicinal Chemistry Research, 1996 , vol. 6, # 6 p. 400 - 411 Title/Abstract Full Text View citing articles Show Details

DOM hydrochloride

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

Kothari; Hathaway; Nichols; Yim

Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 882 - 884 Title/Abstract Full Text View citing articles Show Details

Knittel, James J.; Makriyannis, Alexandros

Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 906 - 909 Title/Abstract Full Text View citing articles Show Details

Shulgin; Dyer

Journal of Medicinal Chemistry, 1975 , vol. 18, # 12 p. 1201 - 1204 Title/Abstract Full Text View citing articles Show Details

1b*HCl

Coutts; Malicky

Canadian Journal of Chemistry, 1974 , vol. 52, # 3 p. 395 - 399 Title/Abstract Full Text View citing articles Show Details

1*HCl

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Patent-Specific Data (1) Location in Patent

Reference

Claim

Luminis Pty Limited

Patent: US6403651 B1, 2002 ; Title/Abstract Full Text Show Details

Physical Data

Melting Point (4) Melting Point

Solvent (Melting Point)

Reference

189 - 190 °C

propan-2-ol

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

189 - 190 °C

diethyl ether

Shulgin; Dyer

Journal of Medicinal Chemistry, 1975 , vol. 18, # 12 p. 1201 - 1204 Title/Abstract Full Text View citing articles Show Details

Coutts; Malicky

Canadian Journal of Chemistry, 1974 , vol. 52, # 3 p. 395 - 399 Title/Abstract Full Text View citing articles Show Details

176 - 178 °C

185 - 188 °C

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

propan-2-ol

Conformation (1) Object of Investigation

Reference

Conformation

Knittel, James J.; Makriyannis, Alexandros

Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 906 - 909 Title/Abstract Full Text View citing articles Show Details

Spectra NMR Spectroscopy (7) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Chemical shifts

Coupling Nuclei

Solvents (NMR Spectroscopy)

Temperature (NMR Spectroscopy)

Frequency (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Reference

tetradeuteriomethanol

300 MHz

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

tetradeuteriomethanol

300 MHz

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

13C

tetradeuteriomethanol

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

Chemical shifts

D2O

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

D2O

Spin-spin coupling constants

Chemical shifts

Spin-lattice relaxation time

13C

D2O

1H-1H

30 °C

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

Knittel, James J.; Makriyannis, Alexandros

Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 906 - 909 Title/Abstract Full Text View citing articles Show Details

Knittel, James J.; Makriyannis, Alexandros

Journal of Medicinal Chemistry, 1981 , vol. 24, #

(T1)

7 p. 906 - 909 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (3) 1 of 3

Comment (Pharmacological Data)

Bioactivities present

Reference

Coutts; Malicky

Canadian Journal of Chemistry, 1974 , vol. 52, # 3 p. 395 - 399 Title/Abstract Full Text View citing articles Show Details

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Shulgin; Dyer

Journal of Medicinal Chemistry, 1975 , vol. 18, # 12 p. 1201 - 1204 Title/Abstract Full Text View citing articles Show Details

Glennon; Liebowitz; Mack

Journal of Medicinal Chemistry, 1978 , vol. 21, # 8 p. 822 - 825 Title/Abstract Full Text View citing articles Show Details

Luminis Pty Limited

Patent: US6403651 B1, 2002 ; Title/Abstract Full Text Show Details

Kothari; Hathaway; Nichols; Yim

Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 882 - 884 Title/Abstract Full Text View citing articles Show Details

Knittel, James J.; Makriyannis, Alexandros

Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 906 - 909 Title/Abstract Full Text View citing articles Show Details

Squella, J. A.; Berguecio, M. A.; Hernandez, A.; Cassels B. K.; Nunez-Vergara, L. J.

Journal de Chimie Physique et de Physico-Chimie Biologique, 1992 , vol. 89, # 3 p. 669 - 680 Title/Abstract Full Text Show Details

Glennon; Titeler; Lyon; Slusher

Journal of Medicinal Chemistry, 1988 , vol. 31, # 4 p. 867 - 870 Title/Abstract Full Text View citing articles Show Details

Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.

Medicinal Chemistry Research, 1996 , vol. 6, # 6 p. 400 - 411 Title/Abstract Full Text View citing articles Show Details

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

May, Jesse A.; Sharif, Najam A.; Chen, Hwang-Hsing; Liao, John C.; Kelly, Curtis R.; Glennon, Richard A.; Young, Richard; Li, JunXu; Rice, Kenner C.; France, Charles P.

Pharmacology Biochemistry and Behavior, 2009 , vol. 91, # 3 p. 307 - 314 Title/Abstract Full Text View citing articles Show Details

Glennon, Richard A.; Dukat, Malgorzata; Grella, Brian; Hong, Seoung-Soo; Costantino, Luca; Teitler, Milt; Smith, Carol; Egan, Chris; Davis, Katherine; Mattson, Mariena V.

Drug and Alcohol Dependence, 2000 , vol. 60, # 2 p. 121 - 132 Title/Abstract Full Text View citing articles Show Details

Knittel; Makriyannis

Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 906 - 909 Title/Abstract Full Text Show Details

Glennon; Young; Rosecrans; Kallman

Psychopharmacology, 1980 , vol. 68, # 2 p. 155 - 158 Title/Abstract Full Text Show Details

SATYA P. GUPTA; PRITHVI SINGH; MAHESH C. BINDAL

Chemical reviews, 1983 , vol. 83, # 6 p. 633 - 649 Title/Abstract Full Text Show Details

2 of 3

Effect (Pharmacological Data)

training drug

Species or TestSystem (Pharmacological Data)

Sprague-Dowley rat

Sex

male

Route of Application

intraperitoneal

Concentration (Pharmacological Data)

1 mg/kg

Exposure Period (Pharmacological

2.5 min

Data)

3 of 3

Method (Pharmacological Data)

15 min after injection of title compound treated with 7-bromo-5,8-dimethoxy-1,2,3,4-tetrahydroisoquinoline HCl, or with 5,8-dimethoxy-7methyl-1,2,3,4-tetrahydroisoquinoline HCl, or with 5,8-dimethoxy-2,7-dimethyl-1,2,3,4-tetrahydroisoquinoline HCl

Results

title compound alone produced 96 percent drug-appropriate responding; cotreatment with 1,2,3,4-tetrahydroisoquinoline derivatives produced maximum 2-5 percent title compound-appropriate responding

Reference

Malmusi, Luca; Dukat, Malgorzata; Young, Richard; Teitler, Milt; Darmani, Nissar A.; Ahmad, Bashir; Smith, Carol; Glennon, Richard A.

Medicinal Chemistry Research, 1996 , vol. 6, # 6 p. 400 - 411 Title/Abstract Full Text View citing articles Show Details

Comment (Pharmacological Data)

serotonin-like activity; rats

Reference

Kothari; Hathaway; Nichols; Yim

Journal of Medicinal Chemistry, 1981 , vol. 24, # 7 p. 882 - 884 Title/Abstract Full Text View citing articles Show Details

Chemical Name: (+)-DOM hydrochloride

no reactions.

Reaxys Registry Number: 6796017

Type of Substance: isocyclic Molecular Formula: C12H19NO2*ClH Linear Structure Formula: C12H19NO2*ClH Molecular Weight: 245.749

InChI Key: IPIMRNFGYPQKAM-FVGYRXGTSA-N 12

Synthesize | Hide Details Find similar Chemical Names and Synonyms (+)-DOM hydrochloride Identification Substance Label (2) Label

Reference

1b*HCl

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (3) Melting Point

Solvent (Melting Point)

Reference

197 °C

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

198 - 200 °C

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

204 - 205 °C

propan-2-ol H2O

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Identification Physical Data (6) Bioactivity (1)

Optical Rotatory Power (3) Type (Optical Rotatory Power)

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

4 g/100ml

H2O

16 deg

589 nm

25 °C

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

[alpha]

2.5 g/100ml

H2O

17.2 deg

589 nm

25 °C

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

[alpha]

2 g/100ml

H2O

17.2 deg

589 nm

25 °C

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Reference

Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Dyer; Nichols; Rusterholz; Barfknecht

Life Sciences, 1973 , vol. 13, # 7 p. 885 - 896 Title/Abstract Full Text Show Details

Chemical Name: (-)-DOM hydrochloride Reaxys Registry Number: 6796018

Type of Substance: isocyclic Molecular Formula: C12H19NO2*ClH Linear Structure Formula: C12H19NO2*ClH Molecular Weight: 245.749

InChI Key: IPIMRNFGYPQKAM-SBSPUUFOSA-N

Synthesize | Hide Details Find similar Chemical Names and Synonyms (-)-DOM hydrochloride, (R)-(-)-2,5-dimethoxy-4-methylamphetamine hydrochloride Identification Substance Label (3) Label

Reference

(R)-5b

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

1a*HCl

Matin,S.B. et al.

no reactions.

Identification Physical Data (7) Bioactivity (1)

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Physical Data Melting Point (3) Melting Point

Solvent (Melting Point)

Reference

196 °C

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

200 - 202 °C

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

propan-2-ol diethyl ether

204 - 205 °C

Optical Rotatory Power (4) Type (Optical Rotatory Power)

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

Optical Rotatory Power

Wavelength (Optical Rotatory Power)

Temperature (Optical Rotatory Power)

[alpha]

1.00 g/100ml

H2O

-16.2 deg

589 nm

22 °C

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

[alpha]

5 g/100ml

H2O

-17 deg

589 nm

25 °C

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

[alpha]

2.5 g/100ml

H2O

-17.6 deg

589 nm

25 °C

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

[alpha]

2 g/100ml

H2O

-17.2 deg

589 nm

25 °C

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

Nichols; Barfknecht; Rusterholz; Benington; Morin

Journal of medicinal chemistry, 1973 , vol. 16, # 5 p. 480 - 483 Title/Abstract Full Text View citing articles Show Details

Matin,S.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 877 - 882 Full Text View citing articles Show Details

Aldous,F.A.B. et al.

Journal of Medicinal Chemistry, 1974 , vol. 17, p. 1100 - 1111 Full Text View citing articles Show Details

Wagner, Jared M.; McElhinny Jr., Charles J.; Lewin, Anita H.; Carroll, F. Ivy

Tetrahedron Asymmetry, 2003 , vol. 14, # 15 p. 2119 - 2125 Title/Abstract Full Text View citing articles Show Details

Dyer; Nichols; Rusterholz; Barfknecht

Life Sciences, 1973 , vol. 13, # 7 p. 885 - 896

Reference

Title/Abstract Full Text Show Details

Reaxys Registry Number: 7278226

Type of Substance: isocyclic Molecular Formula: C12H19NO2*ClH Linear Structure Formula: C12H16(2)H3NO2*ClH

no reactions.

Identification Physical Data (1) Spectra (1)

Molecular Weight: 248.725

InChI Key: IPIMRNFGYPQKAM-NIIDSAIPSA-N

Synthesize | Hide Details Find similar

Identification Substance Label (1) Label

Reference

zu 1-d3

Zweig,J.S.; Castagnoli,N.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 414 - 421 Full Text View citing articles Show Details

Physical Data Melting Point (1) Melting Point

Solvent (Melting Point)

Reference

187 - 189 °C

ethanol

Zweig,J.S.; Castagnoli,N.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 414 - 421 Full Text View citing articles Show Details

Spectra NMR Spectroscopy (1) Description (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Reference

Chemical shifts

Zweig,J.S.; Castagnoli,N.

Journal of Medicinal Chemistry, 1977 , vol. 20, p. 414 - 421 Full Text View citing articles Show Details

Reaxys Registry Number: 25446010

Molecular Formula: C12H19NO2*C12H19NO2

Linear Structure Formula: C12H19NO2*C12H19NO2

Molecular Weight: 418.577

InChI Key: LFEOSNJRMDKHMW-IGXPJQGBSA-N

Synthesize | Hide Details Find similar

Bioactivity Pharmacological Data (1)

no reactions.

Bioactivity (1)

1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

McGraw; Callery; Castagnoli Jr.

Journal of Medicinal Chemistry, 1977 , vol. 20, # 2 p. 185 - 189 Title/Abstract Full Text Show Details

Reaxys Registry Number: 25446386

Molecular Formula: C12H19NO2*C12H19NO2

Linear Structure Formula: C12H17(2)H2NO2*C12H19NO2

no reactions.

Bioactivity (1)

no reactions.

Bioactivity (1)

Molecular Weight: 420.561

InChI Key: LFEOSNJRMDKHMW-WABQDNSHSA-N

Synthesize | Hide Details Find similar

Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

J.S.; Castagnoli Jr. Journal of Medicinal Chemistry, 1977 , vol. 20, # 3 p. 414 - 421 Title/Abstract Full Text Show Details Reaxys Registry Number: 25446387

Molecular Formula: C12H19NO2*C12H19NO2

Linear Structure Formula: C12H17(2)H2NO2*C12H19NO2 Molecular Weight: 420.561

InChI Key: LFEOSNJRMDKHMW-GGAQGYCBSA-N

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Bioactivity Pharmacological Data (1) 1 of 1

Comment (Pharmacological Data)

Bioactivities present

Reference

J.S.; Castagnoli Jr. Journal of Medicinal Chemistry, 1977 , vol. 20, # 3 p. 414 - 421 Title/Abstract Full Text Show Details