Explore 4-Hydroxyamphetamine | PiHKAL · info

Exploring 4-Hydroxyamphetamine. To explore a different substance…

Names

PHA
4-Hydroxyamphetamine
4-OH-A

IUPAC name

4-(2-Aminopropyl)phenol

ID 2148 · Formula C₉H₁₃NO · Molecular weight 151.206

InChI InChI=1S/C9H13NO/c1-7(10)6-8-2-4-9(11)5-3-8/h2-5,7,11H,6,10H2,1H3

InChI Key GIKNHHRFLCDOEU-UHFFFAOYSA-N This stereoisomer Any stereoisomer

SMILES CC(Cc1ccc(cc1)O)N

ChemSpider 3525
PubChem 3651
Wikidata Q5955531
Wikipedia 4-Hydroxyamphetamine
Trout’s Notes α-Methyl-4-hydroxyphenethylamine. In The Cactus Alkaloids (2013, upd. 2018), p. 32

Shulgin Index #109 PHA · Table 3Page 323Row 22

PiHKAL #97 4-MA

Phenethylamine: Von der Strucktur zur Funktion PHA: 6.3 (10) 403

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. https://doi.org/10.1016/j.forsciint.2011.11.003

Foster, BC; Nantais, LM; Wilson, DL; By, AW; Zamecnik, J; Lodge, BA. Fungal metabolism of 4-substituted amphetamines. Xenobiotica, 1 Jan 1990, 20 (6), 583–590. 510 kB. https://doi.org/10.3109/00498259009046873

Buttar, HS; Moffatt, JH; Foster, BC. Developmental toxicity of 4-substituted amphetamines in mice. Reprod. Toxicol., 1 Jul 1996, 10 (4), 301–310. 710 kB. https://doi.org/10.1016/0890-6238(96)00059-7

Warren, RJ; Begosh, PP; Zarembo, JE. Identification of amphetamines and related sympathomimetic amines. J. Assoc. Off. Anal. Chem., , 54 (5), 1179–1191. 3.4 MB. #14 NMR,IR,UV

Horn, AS. Structure-activity relations for the inhibition of catecholamine uptake into synaptosomes from noradrenaline and dopaminergic neurones in rat brain homogenates. Br. J. Pharmacol., 1 Feb 1973, 47 (2), 332–338. 903 kB. https://doi.org/10.1111/j.1476-5381.1973.tb08331.x

Foster, BC; Litster, DL; Lodge, BA. Biotransformation of 2-, 3-, and 4-methoxyamphetamines by Cunninghamella echinulata. Xenobiotica, 1 Jan 1991, 21 (10), 1337–1346. 553 kB. https://doi.org/10.3109/00498259109043208

EMCDDA. New drugs in Europe, 2012, European Monitoring Centre for Drugs and Drug Addiction, Lisbon, 1 May 2013. 773 kB. #51

King, LA. New phenethylamines in Europe. Drug Test. Anal., 1 Jul 2014, 6 (7-8), 808-818. 472 kB. https://doi.org/10.1002/dta.1570

Biel, JH; Bopp, BA. Amphetamines: Structure-activity relationships. In Handbook of Psychopharmacology: Stimulants; Iversen, LL; Iversen, SD; Snyder, SH, Eds., Plenum Press, New York, 1 Jan 1978; pp 1–39. 1.0 MB. https://doi.org/10.1007/978-1-4757-0510-2_1

Abbruscato, TJ; Trippier, PC. DARK classics in chemical neuroscience: Methamphetamine. ACS Chem. Neurosci., 17 Oct 2018, 9 (10), 2373-2378. 393 kB. https://doi.org/10.1021/acschemneuro.8b00123 #pOH-AMP

Clancy, L; Philp, M; Shimmon, R; Fu, S. Development and validation of a color spot test method for the presumptive detection of 25-NBOMe compounds. Drug Test. Anal., 19 Aug 2020, 13 (5), 929-943. 11.3 MB. https://doi.org/10.1002/dta.2905 #4-hydroxyamphetamine

Nakagawasai, O; Arai, Y; Satoh, S; Satoh, N; Neda, M; Hozumi, M; Oka, R; Hiraga, H; Tadano, T. Monoamine oxidase and head-twitch response in mice: Mechanisms of α-methylated substrate derivatives. Neurotoxicology, 1 Jan 2004, 25 (1), 223–232. 169 kB. https://doi.org/10.1016/S0161-813X(03)00101-3 #p-OHA

Philp, M; Shimmon, R; Stojanovska, N; Tahtouh, M; Fu, S. Development and validation of a presumptive colour spot test method for the detection of piperazine analogues in seized illicit materials. Anal. Methods, 1 Jan 2013, 5 (20), 5402. 783 kB. https://doi.org/10.1039/c3ay40511g #4-Hydroxyamphetamine MS,NMR,IR,spot

Benington, F; Morin, RD. The chemorelease of norepinephrine from mouse hearts by substituted amphetamines. J. Med. Chem., 1 Jul 1968, 11 (4), 896–897. 244 kB. https://doi.org/10.1021/jm00310a048 #2.2

4-MPEA · MPEA

3-MPEA · EA-1302

N-Methyltyramine · HMePEA

2-MPEA

3-HA · Gepefrine

Norephedrine

AMPH-OH · HOT-A · NOHA

Cathine · Norpseudoephedrine

N-Me-2-HPEA

2-HA

3-HMPEA

β-Me-HPEA

2,3-HMePEA

10160

PPA · Phenylpropanolamine

Halostachine

β-MeO-PEA

Phenylalaninol

7 Dec 2019 · · Isomer Design