Chlorphentermine

Title: Chlorphentermine
CAS Registry Number: 461-78-9
CAS Name: 4-Chloro-a,a-dimethylbenzeneethanamine
Additional Names: 4-chloro-a,a-dimethylphenethylamine; a,a-dimethyl-p-chlorophenethylamine; 1-(p-chlorophenyl)-2-methyl-2-propylamine; 1-(p-chlorophenyl)-2-methyl-2-aminopropane; clorfentermina
Trademarks: Lucofen (Lundbeck); Teramine (Darby)
Molecular Formula: C10H14ClN
Molecular Weight: 183.68
Percent Composition: C 65.39%, H 7.68%, Cl 19.30%, N 7.63%
Literature References: Prepn: Bachman et al., J. Am. Chem. Soc. 76, 3972 (1954); Ferrari, Farmaco Ed. Sci. 15, 337 (1960); FR M1299 and FR 1296132 (1962 to Simes), C.A. 58, 4467e, 3352g (1963); GB 90633l (1962 to Kefalas), C.A. 58, 6654c (1963). Pharmacology: Jun et al., Can. J. Pharm. Sci. 4, 27 (1969); Ciborska et al., Acta Pol. Pharm. 26, 595 (1969); Moeller-Nielsen, Dubnick, Proc. Int. Symp. Amphetamines Relat. Compounds 1969, E. Costa, Ed. (Raven Press, New York, 1970) pp 63-73.
Properties: Liquid. bp2 100-102°.
Boiling point: bp2 100-102°
Derivative Type: Hydrochloride
CAS Registry Number: 151-06-4
Trademarks: Pre-Sate (Warner-Lambert)
Molecular Formula: C10H14ClN.HCl
Molecular Weight: 220.14
Percent Composition: C 54.56%, H 6.87%, Cl 32.21%, N 6.36%
Properties: Crystals from alcohol + ether, mp 234°. Soly in water: >20%. pH of 1% aq soln ~5.5. LD50 in mice (mg/kg): 270 orally; 267 s.c. (Ciborska).
Melting point: mp 234°
Toxicity data: LD50 in mice (mg/kg): 270 orally; 267 s.c. (Ciborska)
NOTE: This is a controlled substance (stimulant): 21 CFR, 1308.13.
Therap-Cat: Anorexic.
Keywords: Anorexic; CNS Stimulant.
Chlorproethazine Chlorproguanil Chlorpropamide Chlorpropham Chlorprothixene

Chlorphentermine
Chlorphentermine.svg
Systematic (IUPAC) name
1-(4-chlorophenyl)-2-methylpropan-2-amine
Clinical data
Legal status Schedule III (US)
Routes Oral, Insufflated, Rectal
Pharmacokinetic data
Half-life 40 hours
Excretion Renal
Identifiers
CAS number 461-78-9 N 151-06-4
ATC code A08AA
PubChem CID 10007
DrugBank DB01556
ChemSpider 9613 YesY
UNII NHW07912O7 YesY
KEGG C07559 YesY
ChEMBL CHEMBL1201269 N
Synonyms p-Chloro-α,α-dimethylphenethylamine
Chemical data
Formula C10H14ClN 
Mol. mass 183.68 g/mol
 N (what is this?)  (verify)

Chlorphentermine (trade names Apsedon, Desopimon, Lucofen) is an appetite suppressant of the phenethylamine class. Developed in 1962, it is the 4-chloro derivative of the better known appetite suppressant phentermine,[1] which is still in current use.

Chlorphentermine itself is a relatively weak stimulant with little abuse potential, but is classed as a Schedule III drug in the USA due mainly to its similarity to other appetite suppressants such as diethylpropion which have been more widely abused. It is no longer used due mainly to safety concerns, as it has a serotonergic effects profile similar to other withdrawn appetite suppressants such as fenfluramine and aminorex which were found to cause pulmonary hypertension and cardiac fibrosis following prolonged use.[2]