Xylopropamine

Stimulant drug of the phenethylamine and amphetamine classes

none

Legal statusLegal status

CA: Schedule I
UK: Class B
US: Schedule I (positional isomer of Etilamfetamine)
In general: ℞ (Prescription only)

Identifiers

IUPAC name

(±)-1-(3,4-dimethylphenyl)propan-2-amine

CAS Number

102-31-8^N
Sulfate: 14543-76-1^N

PubChem CID

26727

ChemSpider

24901^N

UNII

4DB10V9J2I
Sulfate: B464QNG39U^N

CompTox Dashboard (EPA)

DTXSID70904041

Chemical and physical dataFormulaC₁₁H₁₇NMolar mass163.264 g·mol⁻¹3D model (JSmol)

Interactive image

ChiralityRacemic mixture

SMILES

c1c(ccc(c1C)C)CC(N)C

InChI

InChI=1S/C11H17N/c1-8-4-5-11(6-9(8)2)7-10(3)12/h4-6,10H,7,12H2,1-3H3^N
Key:ZSZUWPRERIPUBM-UHFFFAOYSA-N^N

^NY (what is this?) (verify)

Xylopropamine (Perhedrin, Esanin), also known as 3,4-dimethylamphetamine, is a stimulant drug of the phenethylamine and amphetamine classes which was developed and marketed as an appetite suppressant in the 1950s.^[1]

Xylopropamine was briefly sold as the sulfate salt, but it was not widely marketed. Other related amphetamine derivatives such as 2,4-dimethylamphetamine were also investigated for the same purpose, however these drugs had negative side effects such as high blood pressure and were not very successful, mainly due to the introduction of alternative drugs like phentermine which had similar efficacy but fewer side effects.

Xylopropamine was also reported as having analgesic^[2] and anti-inflammatory^[3] effects but its side effect profile resulted in it never being further developed for these applications.

References

^ US 2384700, Schnider O, "Alkylated phenyl-isopropyl-amines and process for the manufacture of same", issued 11 September 1945, assigned to Hoffman La Roche
^ Harris SC, Worley RC (June 1957). "Analgesic properties of xylopropamine". Proceedings of the Society for Experimental Biology and Medicine. 95 (2): 212–5. doi:10.3181/00379727-95-23170. PMID 13441687. S2CID 34027366.
^ Randall LO, Selitto JJ, Valdes J (December 1957). "Anti-inflammatory effects of xylopropamine". Archives Internationales de Pharmacodynamie et de Therapie. 113 (1–2): 233–49. PMID 13509788.

Stimulants

Adamantanes

Adenosine antagonists

1-(4-Methylphenyl)-2-aminobutane
1-Methylamino-1-(3,4-methylenedioxyphenyl)propane
2-Fluoroamphetamine
2-Fluoromethamphetamine
2-OH-PEA
2-Phenyl-3-aminobutane
2,3-MDA
3-Fluoroamphetamine
3-Fluoroethamphetamine
3-Methoxyamphetamine
3-Methylamphetamine
4-Fluoroamphetamine
4-Fluoromethamphetamine
4-MA
4-MMA
4-MTA
6-FNE
AL-1095
Alfetamine
a-Ethylphenethylamine
Amfecloral
Amfepentorex
Amidephrine
2-Amino-1,2-dihydronaphthalene
2-Aminoindane
5-(2-Aminopropyl)indole
2-Aminotetralin
Acridorex
Amphetamine (Dextroamphetamine, Levoamphetamine)
Amphetaminil
Arbutamine
β-Methylphenethylamine
β-Phenylmethamphetamine
Benfluorex
Benzphetamine
BDB
BOH
3-Benzhydrylmorpholine
BPAP
Camfetamine
Cathine
Chlorphentermine
Cilobamine
Cinnamedrine
Clenbuterol
Clobenzorex
Cloforex
Clortermine
Cypenamine
D-Deprenyl
Denopamine
Dimethoxyamphetamine
Dimethylamphetamine
Dobutamine
DOPA (Dextrodopa, Levodopa)
Dopamine
Dopexamine
Droxidopa
EBDB
Ephedrine
Epinephrine
Epinine
Etafedrine
Ethylnorepinephrine
Etilamfetamine
Etilefrine
Famprofazone
Fencamfamin
Fencamine
Fenethylline
Fenfluramine (Dexfenfluramine, Levofenfluramine)
Fenproporex
Feprosidnine
Fludorex
Formetorex
Furfenorex
Gepefrine
Hexapradol
HMMA
Hordenine
4-Hydroxyamphetamine
5-Iodo-2-aminoindane
Ibopamine
Indanylamphetamine
Iofetamine
Isoetarine
Isoprenaline
L-Deprenyl (Selegiline)
Lefetamine
Lisdexamfetamine
Lophophine
MBDB
MDA (tenamfetamine)
MDBU
MDEA
MDMA (midomafetamine)
MDMPEA
MDOH
MDPR
MDPEA
Mefenorex
Mephentermine
Metanephrine
Metaraminol
Mesocarb
Methamphetamine (Dextromethamphetamine, Levomethamphetamine)
Methoxamine
Methoxyphenamine
MMA
Methoxyphenamine
MMDA
MMDMA
MMMA
Morforex
N,alpha-Diethylphenylethylamine
N,N-Dimethylphenethylamine
Naphthylamphetamine
Nisoxetine
Norepinephrine
Norfenefrine
Norfenfluramine
Normetanephrine
L-Norpseudoephedrine
Octopamine
Orciprenaline
Ortetamine
Oxifentorex
Oxilofrine
PBA
PCA
PCMA
PHA
Pentorex
Phenatine
Phenpromethamine
Phentermine
Phenylalanine
Phenylephrine
Phenylpropanolamine
Pholedrine
PIA
PMA
PMEA
PMMA
PPAP
Prenylamine
Propylamphetamine
Pseudoephedrine
Ropinirole
Salbutamol (Levosalbutamol)
Sibutramine
Solriamfetol
Synephrine
Theodrenaline
Tiflorex
Tranylcypromine
Tyramine
Tyrosine
Xylopropamine
Zylofuramine

Phenylmorpholines

Piperazines

Piperidines

1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine
2-Benzylpiperidine
2-Methyl-3-phenylpiperidine
3,4-Dichloromethylphenidate
4-Benzylpiperidine
4-Fluoromethylphenidate
4-Methylmethylphenidate
Desoxypipradrol
Difemetorex
Diphenylpyraline
Ethylnaphthidate
Ethylphenidate
Methylnaphthidate
Isopropylphenidate
JZ-IV-10
Methylphenidate (Dexmethylphenidate)
Nocaine
Phacetoperane
Pipradrol
Propylphenidate
Serdexmethylphenidate
SCH-5472

Others

Antiobesity agents/Anorectics (A08)

Stimulants

Amphetamines and phenethylamines	4-Methylamphetamine^‡ Amfecloral Amfepentorex Amfepramone Amphetamine Amphetaminil Benzphetamine Cathine Cathinone Chlorphentermine Clobenzorex Cloforex Clortermine Dextroamphetamine Dimethylcathinone Ephedrine Ephedra^‡ Etilamfetamine Etolorex Fenethylline Fenproporex Fludorex Furfenorex^‡ Khat Lisdexamfetamine Mefenorex Methamphetamine Norfenfluramine Pentorex Phentermine (+topiramate) Xylopropamine Zylofuramine
Adrenergic agonists	Albuterol Clenbuterol^§ Ephedrine Ephedra^‡ Levopropylhexedrine Synephrine Terbutaline Yohimbine (Yohimbe)
Other	Aminorex^‡ Atomoxetine Benfluorex^‡ Bupropion (+naltrexone) Dexfenfluramine^‡ Dexmethylphenidate Difemetorex^‡ Fenbutrazate Fenfluramine (+phentermine^‡) Manifaxine Mazindol Methylphenidate Phendimetrazine Phenethylamine Phenmetrazine Phenylpropanolamine Pipradrol Propylhexedrine Pyrovalerone Sibutramine^‡ Tesofensine

Cannabinoid
antagonists

GLP-1, GIP, and / or
glucagon agonists

DACRAs

Cagrilintide (+semaglutide^†)

5-HT2C
receptor agonists

5-HTP
Lorcaserin^‡

Absorption inhibitors

Uncouplers

2,4-Dinitrophenol^‡

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

Monoamine releasing agents

DRAsTooltip Dopamine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP
Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine Levopropylhexedrine

NRAsTooltip Norepinephrine releasing agents

Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine
Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone
Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine
Piperazines: 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP
Others: 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine (Levopropylhexedrine) Tuaminoheptane

SRAsTooltip Serotonin releasing agents

Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI
Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT
Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex
Phenethylamines: 2-Methyl-MDA 4-CAB 4-FA 4-FMA 4-HA 4-MTA 5-APDB 5-Methyl-MDA 6-APDB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA TAP
Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP
Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine
Others: Indeloxazine Viqualine

Others

Monoamine activity enhancers: BPAP
PPAP

DAT modulators: Agonist-like: SoRI-9804
SoRI-20040; Antagonist-like: SoRI-20041

Adrenergic release blockers: Bethanidine
Bretylium
Guanadrel
Guanazodine
Guanethidine
Guanoxan

See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

v t e Phenethylamines
Phenethylamines	Psychedelics: 25B-NBOMe 25C-NBOMe 25D-NBOMe 25I-NBOMe 25N-NBOMe 2C-B 2C-B-AN 2C-Bn 2C-Bu 2C-C 2C-CN 2C-CP 2C-D 2C-E 2C-EF 2C-F 2C-G 2C-G-1 2C-G-2 2C-G-3 2C-G-4 2C-G-5 2C-G-6 2C-G-N 2C-H 2C-I 2C-iP 2C-N 2C-NH2 2C-O 2C-O-4 2C-P 2C-Ph 2C-SE 2C-T 2C-T-2 2C-T-3 2C-T-4 2C-T-5 2C-T-6 2C-T-7 2C-T-8 2C-T-9 2C-T-10 2C-T-11 2C-T-12 2C-T-13 2C-T-14 2C-T-15 2C-T-16 2C-T-17 2C-T-18 2C-T-19 2C-T-20 2C-T-21 2C-T-22 2C-T-22.5 2C-T-23 2C-T-24 2C-T-25 2C-T-27 2C-T-28 2C-T-30 2C-T-31 2C-T-32 2C-T-33 2C-TFE 2C-TFM 2C-YN 2C-V Allylescaline DESOXY Escaline Isoproscaline Jimscaline Macromerine MEPEA Mescaline Metaescaline Methallylescaline Proscaline Psi-2C-T-4 TCB-2 Stimulants: Phenylethanolamine Hordenine Phenethylamine Phenpromethamine α-Methylphenethylamine (amphetamine) β-Methylphenethylamine m-Methylphenethylamine N-Methylphenethylamine o-Methylphenethylamine p-Methylphenethylamine Methylphenidate Entactogens: Lophophine MDPEA MDMPEA Others: BOH DMPEA
Amphetamines	Psychedelics: 3C-AL 3C-BZ 3C-E 3C-MAL 3C-P Aleph Beatrice Bromo-DragonFLY D-Deprenyl DMA DMCPA DMMDA DOB DOC DOEF DOET DOI DOM DON DOPR DOTFM Ganesha MMDA MMDA-2 Psi-DOM TMA TeMA ZDCM-04 Stimulants: 2-FA 2-FMA 3-FA 3-FMA Acridorex Alfetamine Amfecloral Amfepentorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Benfluorex Benzphetamine Cathine Clobenzorex Dimethylamphetamine Ephedrine Etilamfetamine Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Flucetorex Fludorex Formetorex Furfenorex Gepefrine 4-Hydroxyamphetamine Iofetamine Isopropylamphetamine Lefetamine Lisdexamfetamine Mefenorex Metaraminol Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxyphenamine MMA Morforex Norfenfluramine L-Norpseudoephedrine N,alpha-Diethylphenylethylamine Oxifentorex Oxilofrine Ortetamine PBA PCA PFA PFMA PIA PMA PMEA PMMA Phenylpropanolamine Pholedrine Prenylamine Propylamphetamine Pseudoephedrine Sibutramine Tiflorex Tranylcypromine Xylopropamine Zylofuramine Entactogens: 4-FA 4-FMA 4-MA 4-MMA 4-MTA 5-APB 5-APDB 5-EAPB 5-IT 5-MAPB 5-MAPDB 6-APB 6-APDB 6-Chloro-MDMA 6-EAPB 6-IT 6-MAPB 6-MAPDB EDA IAP 2,3-MDA 3,4-MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDOH Methamnetamine MMDMA Naphthylaminopropane TAP Others: 3,4-DCA Amiflamine DiFMDA Selegiline (also D-Deprenyl)
Phentermines	Stimulants: Chlorphentermine Cloforex Clortermine Etolorex Mephentermine Pentorex Phentermine Entactogens: MDPH MDMPH Others: Cericlamine
Cathinones	Stimulants: 3-FMC 4-MC 4-BMC 4-CMC 4-EMC 4-FMC 4-MEC 4-MeMABP 4-MPD Amfepramone Benzedrone Brephedrone Buphedrone Bupropion Cathinone Dimethylcathinone Ethcathinone Eutylone Hydroxybupropion Methcathinone Methedrone NEB N-Ethylhexedrone N-Ethylpentedrone Pentedrone Pentylone Radafaxine Entactogens: 3,4-DMMC 3-MMC Butylone Ethylone Methylone Methylenedioxycathinone Mephedrone
Phenylisobutylamines	Entactogens: 4-CAB 4-MAB Ariadne BDB Butylone EBDB Eutylone MBDB Stimulants: Phenylisobutylamine
Phenylalkylpyrrolidines	Stimulants: α-PBP α-PHP α-PPP α-PVP MDPBP MDPPP MDPV 4-MePBP 4-MePHP 4-MePPP MOPPP MOPVP MPBP MPHP MPPP Naphyrone PEP Prolintane Pyrovalerone
Catecholamines (and close relatives)	6-FNE 6-OHDA a-Me-DA a-Me-TRA Adrenochrome Ciladopa D-DOPA (Dextrodopa) Dimetofrine Dopamine Epinephrine Epinine Etilefrine Ethylnorepinephrine Fenclonine Ibopamine Isoprenaline Isoetarine L-DOPA (Levodopa) L-DOPS (Droxidopa) L-Phenylalanine L-Tyrosine m-Tyramine Metanephrine Metaraminol Metaterol Metirosine Methyldopa N,N-Dimethyldopamine Nordefrin (Levonordefrin) Norepinephrine Norfenefrine (m-Octopamine) Normetanephrine Orciprenaline p-Octopamine p-Tyramine Phenylephrine Synephrine
Miscellaneous	AL-LAD Amidephrine Arbutamine Cafedrine Denopamine Desvenlafaxine Diphenidine Dizocilpine Dobutamine Dopexamine Ephenidine Etafedrine ETH-LAD Famprofazone Fluorolintane Hexapradol IP-LAD Lysergic acid amide Lysergic acid 2-butyl amide Lysergic acid 2,4-dimethylazetidide Lysergic acid diethylamide Methoxamine Methoxphenidine MT-45 PARGY-LAD Phenibut PRO-LAD Pronethalol Salbutamol (Levosalbutamol) Solriamfetol Theodrenaline Thiamphenicol UWA-101 Venlafaxine