Chlorphentermine

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

Chlorphentermine
Clinical data
Other namesp-Chloro-α,α-dimethylphenethylamine
Routes of
administration		Oral, Insufflated, Rectal
ATC code
Legal status
Legal status
Pharmacokinetic data
Elimination half-life40 hours
ExcretionRenal
Identifiers
IUPAC name
  • 1-(4-chlorophenyl)-2-methylpropan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.006.651
Chemical and physical data
FormulaC10H14ClN
Molar mass183.68 g·mol−1
3D model (JSmol)
SMILES
  • Clc1ccc(cc1)CC(N)(C)C
InChI
  • InChI=1S/C10H14ClN/c1-10(2,12)7-8-3-5-9(11)6-4-8/h3-6H,7,12H2,1-2H3 Y
  • Key:ZCKAMNXUHHNZLN-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Chlorphentermine acts as a highly selective serotonin releasing agent (SRA).[2] It is not a psychostimulant and has little or no 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 It is no longer used due mainly to safety concerns, as it has a serotonergic effects profile similar to other withdrawn appetite suppressants such as fenfluramine and aminorex which were found to cause pulmonary hypertension and cardiac fibrosis following prolonged use.[3]

The plasma half-life is about five days.[4] It was withdrawn from the market in the UK in 1974.[4]

See also

References
  1. Gylys JA, Hart JJ, Warren MR (September 1962). "Chlorphentermine, a new anorectic agent". The Journal of Pharmacology and Experimental Therapeutics. 137: 365–73. PMID 13903304.
  2. Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, Partilla JS (January 2001). "Amphetamine-type central nervous system stimulants release norepinephrine more potently than they release dopamine and serotonin". Synapse. 39 (1): 32–41. doi:10.1002/1098-2396(20010101)39:1<32::AID-SYN5>3.0.CO;2-3. PMID 11071707. S2CID 15573624.
  3. Rothman RB, Ayestas MA, Dersch CM, Baumann MH (August 1999). "Aminorex, fenfluramine, and chlorphentermine are serotonin transporter substrates. Implications for primary pulmonary hypertension". Circulation. 100 (8): 869–75. doi:10.1161/01.cir.100.8.869. PMID 10458725.
  4. Craddock D (1976). "Anorectic drugs: use in general practice". Drugs. 11 (5): 378–93. doi:10.2165/00003495-197611050-00002. PMID 782835. S2CID 25704474.
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