Trecadrine

Trecadrine (INNTooltip International Nonproprietary Name) is a drug that was originally developed as an anti-ulcer agent but was found to act as a β₃-adrenergic receptor agonist with potential anti-obesity and anti-diabetic properties.^[2][3][1][4] It is selective for the β₃-adrenergic receptor, lacking activity at the β₁- and β₂-adrenergic receptors.^[1] The drug is orally active.^[1] Structurally, trecadrine is a substituted β-hydroxyamphetamine and derivative of β-hydroxy-N-methylamphetamine (ephedrine, pseudoephedrine) with a tricyclic moiety attached at the amine.^[2][5]

Trecadrine

Clinical data
Routes of administration	Oral[1]
Drug class	Sympathomimetic; β3-Adrenergic receptor agonist
Identifiers
IUPAC name 2-[methyl-[2-(2-tricyclo[9.4.0.03,8]pentadeca-1(15),3,5,7,11,13-hexaenylidene)ethyl]amino]-1-phenylpropan-1-ol
CAS Number	90845-56-0
PubChem CID	65823
ChemSpider	59235
UNII	34H206R8A5
CompTox Dashboard (EPA)	DTXSID50869068
Chemical and physical data
Formula	C27H29NO
Molar mass	383.535 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C(C1=CC=CC=C1)O)N(C)CC=C2C3=CC=CC=C3CCC4=CC=CC=C42
InChI InChI=1S/C27H29NO/c1-20(27(29)23-12-4-3-5-13-23)28(2)19-18-26-24-14-8-6-10-21(24)16-17-22-11-7-9-15-25(22)26/h3-15,18,20,27,29H,16-17,19H2,1-2H3 Key:BHVGOYREXHCFOE-UHFFFAOYSA-N