Meptazinol

Meptazinol

Clinical data
AHFS/Drugs.com	International Drug Names
Dependence liability	Low
Routes of administration	Oral, IM, IV
ATC code	N02AX05 (WHO)
Legal status
Legal status	AU: S4 (Prescription only) UK: POM (Prescription only)
Pharmacokinetic data
Metabolism	The peak analgesic effect is seen within 30–60 minutes and lasts about 3–4 hours.
Biological half-life	Half-Life (1.4–4 hours).
Excretion	The drug is rapidly metabolised to the glucuronide, and mostly excreted in the urine.
Identifiers
IUPAC name (RS)-3-(3-ethyl-1-methylazepan-3-yl)phenol
CAS Number	59263-76-2 N
PubChem (CID)	41049
ChemSpider	37469 Y
UNII	18Y7S5JKZD Y
KEGG	D08182 Y
ChEMBL	CHEMBL314437 Y
ECHA InfoCard	100.053.718
Chemical and physical data
Formula	C15H23NO
Molar mass	233.34922 g/mol
3D model (Jmol)	Interactive image
Chirality	Racemic mixture
SMILES OC1=CC=CC(C2(CCCCN(C2)C)CC)=C1
InChI InChI=1S/C15H23NO/c1-3-15(9-4-5-10-16(2)12-15)13-7-6-8-14(17)11-13/h6-8,11,17H,3-5,9-10,12H2,1-2H3 Y Key:JLICHNCFTLFZJN-UHFFFAOYSA-N Y
NY (what is this?)

Meptazinol (trade name Meptid) is an opioid analgesic developed by Wyeth in the 1970s. Indications for use in moderate to severe pain, most commonly used to treat pain in obstetrics (childbirth).

Meptazinol is a 3-phenylazpane derivative, whereas the other phenazepanes like ethoheptazine and proheptazine are 4-phenylazepanes.

A partial µ-opioid receptor agonist, its mixed agonist/antagonist activity affords it a lower risk of dependence and abuse than full µ agonists like morphine. Meptazinol exhibits not only a short onset of action, but also a shorter duration of action relative to other opioids such as morphine, pentazocine, or buprenorphine.