Guineesine

Guineesine

Chemical structure of guineesine
Clinical data
Other names	Guineensine; UNII-7DK8DMU9JX
Identifiers
IUPAC name (2E,4E,12E)-13-(1,3-benzodioxol-5-yl)-N-(2-methylpropyl)trideca-2,4,12-trienamide
CAS Number	55038-30-7
PubChem CID	6442405
ChemSpider	4946489
UNII	7DK8DMU9JX
ChEBI	CHEBI:181825
ChEMBL	ChEMBL404184
Chemical and physical data
Formula	C24H33NO3
Molar mass	383.532 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)CNC(=O)/C=C/C=C/CCCCCC/C=C/C1=CC2=C(C=C1)OCO2
InChI InChI=1S/C24H33NO3/c1-20(2)18-25-24(26)14-12-10-8-6-4-3-5-7-9-11-13-21-15-16-22-23(17-21)28-19-27-22/h8,10-17,20H,3-7,9,18-19H2,1-2H3,(H,25,26)/b10-8+,13-11+,14-12+ Key:FPMPOFBEYSSYDQ-AUVZEZIHSA-N

Guineesine (or guineensine) is a compound isolated from long pepper (Piper longum) and black pepper (Piper nigrum).

Research

Guineensine inhibits the cellular reuptake of anandamide and 2-arachidonoylglycerol in a mouse model (EC₅₀ = 290 nM). This causes an increase in the activity of the two neurotransmitters which are classified as endogenous cannabinoids.

Guineesine can dose-dependently produce cannabimimetic effects in a mouse model which are indicated by potent catatonic, analgesic, hypo-locomotive and hypo-thermic effects. In addition, the analgesic and catatonic effects were reversed by the cannabinoid receptor type 1 (CB1) inverse agonist rimonabant.

Guineesine is also a monoamine oxidase inhibitor (MAOI) in vitro (IC₅₀ = 139.2 μM).

Guineesine(Guineensine) was first isolated,studied and named from Piper guineense Schum and Thonn.[1,2] 1. OKOGUN, J.I. and Ekong, D.E.U. 1974 Extracts from the Fruits of the Piper guineense. Schum and Thonn. J. Chem. Soc. Perkin Transactions I, 1974, 2195-2198. 2. Okwute, S.K. OKOGUN, J.I. and Okorie, D.A. 1984 Revised Structure and Synthesis of Piperolein acids; Guineensine and Wisanine from Piper guineense, TETRAHEDRON, 40, 2541-2545.