Prenylamine

Prenylamine

Systematic (IUPAC) name
(RS)-N-(1-methyl-2-phenylethyl)-3,3-diphenylpropan-1-amine
Clinical data
Routes of administration	Oral
Legal status	Uncontrolled
Identifiers
CAS Number	390-64-7
ATC code	C01DX02 (WHO)
PubChem	CID 9801
ChemSpider	9418
UNII	K2OH82Z000
ChEMBL	CHEMBL24072
Synonyms	N-(3,3-diphenylpropyl)amphetamine
Chemical data
Formula	C24H27N
Molar mass	329.48 g/mol
SMILES CC(Cc1ccccc1)NCCC(c2ccccc2)c3ccccc3
InChI InChI=1S/C24H27N/c1-20(19-21-11-5-2-6-12-21)25-18-17-24(22-13-7-3-8-14-22)23-15-9-4-10-16-23/h2-16,20,24-25H,17-19H2,1H3 Key:IFFPICMESYHZPQ-UHFFFAOYSA-N
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Prenylamine (Segontin) is a calcium channel blocker of the amphetamine chemical class which is used as a vasodilator in the treatment of angina pectoris. It has been shown to partially metabolize to amphetamine and can cause false positives for it in drug tests.^[1][2][3] Prenylamine also appears to act as a vesicular monoamine transporter inhibitor, and has been demonstrated to deplete vesicular monoamine neurotransmitter stores similarly to reserpine.^[4]

References

1. Kraemer T, Roditis SK, Peters FT, Maurer HH (March 2003). "Amphetamine concentrations in human urine following single-dose administration of the calcium antagonist prenylamine-studies using fluorescence polarization immunoassay (FPIA) and GC-MS". Journal of Analytical Toxicology 27 (2): 68–73. doi:10.1093/jat/27.2.68. PMID 12669999.
2. Musshoff F (February 2000). "Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine". Drug Metabolism Reviews 32 (1): 15–44. doi:10.1081/DMR-100100562. PMID 10711406.
3. Cody JT (May 2002). "Precursor medications as a source of methamphetamine and/or amphetamine positive drug testing results". Journal of Occupational and Environmental Medicine / American College of Occupational and Environmental Medicine 44 (5): 435–50. doi:10.1097/00043764-200205000-00012. PMID 12024689.
4. Bagchi SP (1990). "Antidopaminergic action of verapamil and several other drugs: inactivation of vesicular dopamine". Life Sciences 46 (12): 857–63. doi:10.1016/0024-3205(90)90115-8. PMID 1969603.