Chlorphentermine

Chlorphentermine
Clinical data
Other names4-Chlorophentermine; 4-Chloro-α-methylamphetamine; 4-Chloro-α,α-dimethylphenethylamine
Routes of
administration		Oral
Drug classSerotonin releasing agent; Anorectic
ATC code
Legal status
Legal status
  • BR: Class A3 (Psychoactive drugs)[1]
  • CA: Schedule IV
  • UK: Class C
  • US: Schedule III (but withdrawn from the market)
Pharmacokinetic data
Elimination half-life40 hours[2]–5 days[3]
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
  (verify)

Chlorphentermine, sold under the brand names Apsedon, Desopimon, and Lucofen, is a serotonergic appetite suppressant of the amphetamine family. Developed in 1962, it is the para-chloro derivative of the better-known appetite suppressant phentermine, which is still in current use.

The drug acts as a highly selective serotonin releasing agent (SRA).[4] It is not a psychostimulant and has little or no misuse potential, but is classed as a Schedule III drug in the United States due mainly to its similarity to other appetite suppressants such as diethylpropion which have been more widely misused. It is no longer used due mainly to safety concerns, as it has a serotonergic effects profile similar to other withdrawn appetite suppressants such as fenfluramine and aminorex which were found to cause pulmonary hypertension and cardiac fibrosis following prolonged use.[5]

Chlorphentermine was first synthesized by 1954 and was subsequently developed in the early 1960s.[6][7][8][9] It remained on the market in the United States as late as 2004.[10]

  1. ^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. ^ "Chlorphentermine: Uses, Interactions, Mechanism of Action". DrugBank Online. 31 July 2007. Retrieved 4 November 2024.
  3. ^ Cite error: The named reference Craddock1976 was invoked but never defined (see the help page).
  4. ^ Rothman RB, Baumann MH, Dersch CM, Romero DV, Rice KC, Carroll FI, et al. (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.
  5. ^ 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): 869–875. doi:10.1161/01.cir.100.8.869. PMID 10458725.
  6. ^ Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference GylysHartWarren1962 was invoked but never defined (see the help page).
  8. ^ Cite error: The named reference LuceyHadden1962 was invoked but never defined (see the help page).
  9. ^ Cite error: The named reference Fineberg1962 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference IndexNominum2004 was invoked but never defined (see the help page).
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