Phentermine

Phentermine

Clinical data
Trade names	Adipex-p, Duromine, Metermine, Suprenza
AHFS/Drugs.com	Monograph
MedlinePlus	a682187
License data	US FDA: Phentermine
Pregnancy category	AU: B3 US: X (Contraindicated)
Dependence liability	Low
Addiction liability	Very low
Routes of administration	by mouth
ATC code	A08AA01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) CA: Schedule IV DE: Anlage III (Prescription only) US: Schedule IV
Pharmacokinetic data
Bioavailability	High (almost complete)
Protein binding	Approximately 96.3%
Metabolism	Hepatic
Biological half-life	25 hours, urinary pH-dependent
Excretion	Urinary (62–85% unchanged)
Identifiers
IUPAC name 2-methyl-1-phenylpropan-2-amine
Synonyms	α-methyl-amphetamine α,α-dimethylphenethylamine
CAS Number	122-09-8 Y
PubChem (CID)	4771
IUPHAR/BPS	7269
DrugBank	DB00191 Y
ChemSpider	4607 Y
UNII	C045TQL4WP Y
KEGG	D05458 Y
ChEBI	CHEBI:8080 Y
ChEMBL	CHEMBL1574 Y
ECHA InfoCard	100.004.112
Chemical and physical data
Formula	C10H15N
Molar mass	149.233 g/mol
3D model (Jmol)	Interactive image
SMILES NC(Cc1ccccc1)(C)C
InChI InChI=1S/C10H15N/c1-10(2,11)8-9-6-4-3-5-7-9/h3-7H,8,11H2,1-2H3 Y Key:DHHVAGZRUROJKS-UHFFFAOYSA-N Y

Phentermine (α,α-Dimethylphenethylamine), a contraction of "phenyl-tertiary-butylamine", is a psychostimulant drug of the substituted amphetamine chemical class, with pharmacology similar to amphetamine. It is used medically as an appetite suppressant for short term use, as an adjunct to exercise and reducing calorie intake.

It has cardiovascular, gastrointestinal, and CNS side effects; rare cases of pulmonary hypertension and cardiac valvular disease have been reported. It should not be used by people who have a history of drug abuse, have any cardiovascular disease, hyperthyroidism, glaucoma, peptic ulcers, prostatic hypertrophy, or epilepsy, or are pregnant, planning to become pregnant, or breast-feeding. It should not be taken by anyone taking a monoamine oxidase inhibitor, and people should not drink alcohol while they are taking it.

It was first introduced in 1959, and became part of the drug combination Fen-phen that was withdrawn from the market in 1997 due to the fenfluramine component damaging people's heart valves. In 2012 a different combination drug, phentermine/topiramate was approved in the US.