Xylopropamine

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

Trade namesPerhedrin, Esanin

Other names3,4-Dimethylamphetamine; DMeA

Routes of
administrationOral

Drug classStimulant; Appetite suppressant

Quick facts Clinical data, Trade names ...

Xylopropamine

Clinical data
Trade names	Perhedrin, Esanin
Other names	3,4-Dimethylamphetamine; DMeA
Routes of administration	Oral
Drug class	Stimulant; Appetite suppressant
ATC code	None
Legal status
Legal 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 data
Formula	C11H17N
Molar mass	163.264 g·mol−1
3D model (JSmol)	Interactive image
Chirality	Racemic 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)

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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.