Exploring Ephedrine. To explore a different substance…

Ephedrine
Names:
Ephedrine · (1R,2S)-2-Methylamino-1-phenylpropan-1-ol
IUPAC name:
(1R,2S)-2-(Methylamino)-1-phenylpropan-1-ol
ID: 2000 · Formula: C10H15NO · Molecular weight: 165.232
InChI: InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10-/m0/s1

Glennon, RA; Young, R; Martin, BR; Dal Cason, TA. Methcathinone (“Cat”): An enantiomeric potency comparison. Pharmacol. Biochem. Behav., 1 Jan 1995, 50 (4) 601–606. 709 kB. http://dx.doi.org/10.1016/0091-3057(94)00348-3

LeBelle, MJ; Savard, C; Dawson, BA; Black, DB; Katyal, LK; Zrcek, F; By, AW. Chiral identification and determination of ephedrine, pseudoephedrine, methamphetamine and metecathinone by gas chromatography and nuclear magnetic resonance. Forensic Sci. Int., 28 Feb 1995, 71 (3), 215–223. 405 kB. http://dx.doi.org/10.1016/0379-0738(94)01669-0

Nakanishi, K; Miki, A; Zaitsu, K; Kamata, H; Shima, N; Kamata, T; Katagi, M; Tatsuno, M; Tsuchihashi, H; Suzuki, K. Cross-reactivities of various phenethylamine-type designer drugs to immunoassays for amphetamines, with special attention to the evaluation of the one-step urine drug test Instant-View™, and the Emit® assays for use in drug enforcement. Forensic Sci. Int., 10 Apr 2012, 217 (1–3), 174–181. 397 kB. http://dx.doi.org/10.1016/j.forsciint.2011.11.003

Rothman, RB; Vu, N; Partilla, JS; Roth, BL; Hufeisen, SJ; Compton-Toth, BA; Birkes, J; Young, R; Glennon, RA. In vitro characterization of ephedrine-related stereoisomers at biogenic amine transporters and the receptorome reveals selective actions as norepinephrine transporter substrates. J. Pharmacol. Exp. Ther., 1 Oct 2003, 307 (1), 138–145. 516 kB. http://dx.doi.org/10.1124/jpet.103.053975

de Burnaga Sanchez, MJS. Sur un homologue de l’éphédrine. Bull. Soc. Chim. Fr., 1929, 45, 284–286. 600 kB.

Krawczeniuk, AS. Identification of phenethylamines and methylenedioxyamphetamines using liquid chromatography atmospheric pressure electrospray ionization mass spectrometry. Microgram J., 1 Jan 2005, 3 (1–2), 78–100. 979 kB.

Lurie, IS; Bozenko, JS; Li, L; Miller, EE; Greenfield, SJ. Chiral separation of methamphetamine and related compounds using capillary electrophoresis with dynamically coated capillaries. Microgram J., 1 Jan 2011, 8 (1), 24–28. 786 kB.

Norephedrine
Norephedrine
N-Methylephedrine
N-Methylephedrine
METHCATH · Methcathinone
METHCATH; Methcathinone
Cathinone
Cathinone
α-PPP
α-PPP; α-Pyrrolidinopropiophenone
2-AI
2-AI; 2,3-Dihydro-1H-inden-2-amine
2-AT
2-AT; 2-Aminotetralin
PP
PP; 1-Phenylpiperazine
MBZP
MBZP; 1-Benzyl-4-methylpiperazine
BZP
BZP; 1-Benzylpiperazine
1-PEA · α-PEA
1-PEA; 1-Phenylethan-1-amine
Benzylamine
Benzylamine; 1-Phenylmethanamine
homo-PEA
homo-PEA; 3-Phenylpropan-1-amine
pip-PEA
pip-PEA; 1-(2-Phenylethyl)piperidine
AA
AA; 2-Amino-1-phenylethanone
MAA
MAA; 2-(Methylamino)-1-phenylethanone
Phenmetrazine
Phenmetrazine
PIAP
PIAP; 1-Phenyl-2-(piperidin-1-yl)propan-1-one
PZAP
PZAP; 2-(4-Methylpiperazin-1-yl)-1-phenylpropan-1-one
cPr-PEA
cPr-PEA; 2-Phenylcyclopropanamine
bk-2-AT
bk-2-AT; 2-Amino-3,4-dihydronaphthalen-1(2H)-one
2463
1-(3,4-Dihydronaphthalen-1-yl)methanamine
2465
1-(2H-Chromen-4-yl)methanamine
2-ADN
2-ADN; 1,2-Dihydronaphthalen-2-amine
Aminorex
Aminorex
4-MAR · 4-Methylaminorex
4-MAR; 4-Methylaminorex
Phendimetrazine
Phendimetrazine
P2P
P2P; 1-Phenylpropan-2-one
1141
Prop-2-en-1-ylbenzene
1307
6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine
N-Methyl-2-aminotetralin
N-Methyl-2-aminotetralin
NM-2-AI
NM-2-AI; N-Methyl-2-aminoindane
Cyclazodone
Cyclazodone
Fenozolone
Fenozolone
Pemoline
Pemoline
Thozalinone
Thozalinone
N-M-1-PEA
N-M-1-PEA; N-Methyl-1-phenylethan-1-amine
1471
2-Phenylcyclobutanamine
1482
N-Methyl-2-phenylcyclopropanamine
1497
2-Methyl-2-phenylcyclopropanamine
1498
1-Methyl-2-phenylcyclopropanamine
1499
2,2-Diphenylcyclopropanamine
1500
2-Methyl-3-phenylcyclopropanamine
1502
2,3-Diphenylcyclopropanamine
1511
1-Benzylcyclopropanamine
1512
1-Benzyl-N-methylcyclopropanamine
2759
N′-[4-(Dimethylamino)-2-methoxy-5-nitrobenzyl]-N,N-diethylethane-1,2-diamine
Levamisole
Levamisole
Homoamphetamine
Homoamphetamine
W-15
W-15; 4-Chloro-N-[(2E)-1-(2-phenylethyl)piperidin-2-ylidene]benzenesulfonamide
N-Et-Benzylamine
N-Et-Benzylamine
Propargylpemoline
Propargylpemoline
10846
2-(Dimethylamino)-5-methyl-5-phenyl-1,3-oxazol-4(5H)-one
10825
2-Fluoro-2-phenylcyclopropan-1-amine
10824
2-Fluoro-3-phenylcyclopropan-1-amine
723
N-Phenyl-N′-[3-(1-phenylpropan-2-yl)-1,2,3-oxadiazol-3-ium-5-yl]carbamimidate
Priatan
Priatan
Pseudoephedrine
Pseudoephedrine
Phenylpropanolmethylamine
Phenylpropanolmethylamine
PMA
PiHKAL#97 4-MA; SI#110 PMA
2-MA
2-MA; 2-Methoxyamphetamine
3-MA
3-MA; 3-Methoxyamphetamine
Hordenine
Hordenine
β-Methoxyamphetamine
β-Methoxyamphetamine
4-Methylnorephedrine
4-Methylnorephedrine
β-HO-N,N-Me-PEA
β-HO-N,N-Me-PEA; 2-(Dimethylamino)-1-phenylethanol
N,N-Me-2-HPEA
N,N-Me-2-HPEA; 2-[2-(Dimethylamino)ethyl]phenol
2-HMA
2-HMA; 2-[2-(Methylamino)propyl]phenol
N-Me-2-MPEA
N-Me-2-MPEA; 2-(2-Methoxyphenyl)-N-methylethan-1-amine
β-Me-2-MPEA
β-Me-2-MPEA; 2-(2-Methoxyphenyl)propan-1-amine
N,N-Me-3-HPEA
N,N-Me-3-HPEA; 3-[2-(Dimethylamino)ethyl]phenol
N-Me-3-MPEA
N-Me-3-MPEA; 2-(3-Methoxyphenyl)-N-methylethan-1-amine
β-Me-3-MPEA
β-Me-3-MPEA; 2-(3-Methoxyphenyl)propan-1-amine
Pholedrine
Pholedrine
α-Et-4-HPEA
α-Et-4-HPEA; 4-(2-Aminobutyl)phenol
N-Me-4-MPEA
N-Me-4-MPEA; 2-(4-Methoxyphenyl)-N-methylethan-1-amine
β-Me-4-MPEA
β-Me-4-MPEA; 2-(4-Methoxyphenyl)propan-1-amine
4-EPEA
4-EPEA; 2-(4-Ethoxyphenyl)ethan-1-amine
2,3-HMeMPEA
2,3-HMeMPEA; 2-Methyl-6-[2-(methylamino)ethyl]phenol
2,3-HMeA
2,3-HMeA; 2-(2-Aminopropyl)-6-methylphenol
2,4-MMPEA
2,4-MMPEA; 2-(2-Methoxy-4-methylphenyl)ethan-1-amine
β-HO-3,4-MePEA
β-HO-3,4-MePEA; 2-Amino-1-(3,4-dimethylphenyl)ethanol
3,4-HMeA
3,4-HMeA; 5-(2-Aminopropyl)-2-methylphenol
10090
2-(2-Methoxy-5-methylphenyl)ethan-1-amine
10111
3-(2-Aminopropyl)-4-methylphenol
N-MeO-A
N-MeO-A; N-Methoxyamphetamine
4-Me-HOT-A
4-Me-HOT-A; N-Hydroxy-4-methylamphetamine
Ethyltyramine
Ethyltyramine
10158
2-(4-Methoxy-3-methylphenyl)ethan-1-amine
10143
5-(2-Aminopropyl)-2-methylphenol
Norephedrine
Norephedrine
N-Methylephedrine
N-Methylephedrine
METHCATH · Methcathinone
METHCATH; Methcathinone
Cathinone
Cathinone
α-PPP
α-PPP; α-Pyrrolidinopropiophenone
2-AI
2-AI; 2,3-Dihydro-1H-inden-2-amine
2-AT
2-AT; 2-Aminotetralin
PP
PP; 1-Phenylpiperazine
MBZP
MBZP; 1-Benzyl-4-methylpiperazine
BZP
BZP; 1-Benzylpiperazine
1-PEA · α-PEA
1-PEA; 1-Phenylethan-1-amine
Benzylamine
Benzylamine; 1-Phenylmethanamine
homo-PEA
homo-PEA; 3-Phenylpropan-1-amine
pip-PEA
pip-PEA; 1-(2-Phenylethyl)piperidine
AA
AA; 2-Amino-1-phenylethanone
MAA
MAA; 2-(Methylamino)-1-phenylethanone
Phenmetrazine
Phenmetrazine
PIAP
PIAP; 1-Phenyl-2-(piperidin-1-yl)propan-1-one
PZAP
PZAP; 2-(4-Methylpiperazin-1-yl)-1-phenylpropan-1-one
cPr-PEA
cPr-PEA; 2-Phenylcyclopropanamine
bk-2-AT
bk-2-AT; 2-Amino-3,4-dihydronaphthalen-1(2H)-one
2463
1-(3,4-Dihydronaphthalen-1-yl)methanamine
2465
1-(2H-Chromen-4-yl)methanamine
2-ADN
2-ADN; 1,2-Dihydronaphthalen-2-amine
Aminorex
Aminorex
4-MAR · 4-Methylaminorex
4-MAR; 4-Methylaminorex
Phendimetrazine
Phendimetrazine
P2P
P2P; 1-Phenylpropan-2-one
1141
Prop-2-en-1-ylbenzene
1307
6,7,8,9-Tetrahydro-5H-benzo[7]annulen-6-amine
N-Methyl-2-aminotetralin
N-Methyl-2-aminotetralin
NM-2-AI
NM-2-AI; N-Methyl-2-aminoindane
Cyclazodone
Cyclazodone
Fenozolone
Fenozolone
Pemoline
Pemoline
Thozalinone
Thozalinone
N-M-1-PEA
N-M-1-PEA; N-Methyl-1-phenylethan-1-amine
1471
2-Phenylcyclobutanamine
1482
N-Methyl-2-phenylcyclopropanamine
1497
2-Methyl-2-phenylcyclopropanamine
1498
1-Methyl-2-phenylcyclopropanamine
1499
2,2-Diphenylcyclopropanamine
1500
2-Methyl-3-phenylcyclopropanamine
1502
2,3-Diphenylcyclopropanamine
1511
1-Benzylcyclopropanamine
1512
1-Benzyl-N-methylcyclopropanamine
2759
N′-[4-(Dimethylamino)-2-methoxy-5-nitrobenzyl]-N,N-diethylethane-1,2-diamine
Levamisole
Levamisole
Homoamphetamine
Homoamphetamine
W-15
W-15; 4-Chloro-N-[(2E)-1-(2-phenylethyl)piperidin-2-ylidene]benzenesulfonamide
N-Et-Benzylamine
N-Et-Benzylamine
Propargylpemoline
Propargylpemoline
10846
2-(Dimethylamino)-5-methyl-5-phenyl-1,3-oxazol-4(5H)-one
10825
2-Fluoro-2-phenylcyclopropan-1-amine
10824
2-Fluoro-3-phenylcyclopropan-1-amine
723
N-Phenyl-N′-[3-(1-phenylpropan-2-yl)-1,2,3-oxadiazol-3-ium-5-yl]carbamimidate
Priatan
Priatan
Pseudoephedrine
Pseudoephedrine
Phenylpropanolmethylamine
Phenylpropanolmethylamine
PMA
PiHKAL#97 4-MA; SI#110 PMA
2-MA
2-MA; 2-Methoxyamphetamine
3-MA
3-MA; 3-Methoxyamphetamine
Hordenine
Hordenine
β-Methoxyamphetamine
β-Methoxyamphetamine
4-Methylnorephedrine
4-Methylnorephedrine
β-HO-N,N-Me-PEA
β-HO-N,N-Me-PEA; 2-(Dimethylamino)-1-phenylethanol
N,N-Me-2-HPEA
N,N-Me-2-HPEA; 2-[2-(Dimethylamino)ethyl]phenol
2-HMA
2-HMA; 2-[2-(Methylamino)propyl]phenol
N-Me-2-MPEA
N-Me-2-MPEA; 2-(2-Methoxyphenyl)-N-methylethan-1-amine
β-Me-2-MPEA
β-Me-2-MPEA; 2-(2-Methoxyphenyl)propan-1-amine
N,N-Me-3-HPEA
N,N-Me-3-HPEA; 3-[2-(Dimethylamino)ethyl]phenol
N-Me-3-MPEA
N-Me-3-MPEA; 2-(3-Methoxyphenyl)-N-methylethan-1-amine
β-Me-3-MPEA
β-Me-3-MPEA; 2-(3-Methoxyphenyl)propan-1-amine
Pholedrine
Pholedrine
α-Et-4-HPEA
α-Et-4-HPEA; 4-(2-Aminobutyl)phenol
N-Me-4-MPEA
N-Me-4-MPEA; 2-(4-Methoxyphenyl)-N-methylethan-1-amine
β-Me-4-MPEA
β-Me-4-MPEA; 2-(4-Methoxyphenyl)propan-1-amine
4-EPEA
4-EPEA; 2-(4-Ethoxyphenyl)ethan-1-amine
2,3-HMeMPEA
2,3-HMeMPEA; 2-Methyl-6-[2-(methylamino)ethyl]phenol
2,3-HMeA
2,3-HMeA; 2-(2-Aminopropyl)-6-methylphenol
2,4-MMPEA
2,4-MMPEA; 2-(2-Methoxy-4-methylphenyl)ethan-1-amine
β-HO-3,4-MePEA
β-HO-3,4-MePEA; 2-Amino-1-(3,4-dimethylphenyl)ethanol
3,4-HMeA
3,4-HMeA; 5-(2-Aminopropyl)-2-methylphenol
10090
2-(2-Methoxy-5-methylphenyl)ethan-1-amine
10111
3-(2-Aminopropyl)-4-methylphenol
N-MeO-A
N-MeO-A; N-Methoxyamphetamine
4-Me-HOT-A
4-Me-HOT-A; N-Hydroxy-4-methylamphetamine
Ethyltyramine
Ethyltyramine
10158
2-(4-Methoxy-3-methylphenyl)ethan-1-amine
10143
5-(2-Aminopropyl)-2-methylphenol
31 August 2016 · Creative Commons BY-NC-SA ·