Phenylacetylrinvanil

Phenylacetylrinvanil
Identifiers
	IUPAC name [(Z,7R)-18-[(4-Hydroxy-3-methoxyphenyl)methylamino]-18-oxooctadec-9-en-7-yl] 2-phenylacetate;
CAS Number	849343-53-9;
PubChem CID	25171466;
ChemSpider	74098843;
Chemical and physical data
Formula	C34H49NO5
Molar mass	551.768 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCC[C@H](C/C=C\CCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC)OC(=O)CC2=CC=CC=C2;
	InChI InChI=1S/C34H49NO5/c1-3-4-5-15-20-30(40-34(38)26-28-18-13-12-14-19-28)21-16-10-8-6-7-9-11-17-22-33(37)35-27-29-23-24-31(36)32(25-29)39-2/h10,12-14,16,18-19,23-25,30,36H,3-9,11,15,17,20-22,26-27H2,1-2H3,(H,35,37)/b16-10-/t30-/m1/s1; Key:LXLBUUJANYSIKU-DJVRBGHSSA-N;

Phenylacetylrinvanil (IDN-5890) is a synthetic analogue of capsaicin which acts as a potent and selective agonist for the TRPV1 receptor, with slightly lower potency than resiniferatoxin, though still around 300 times the potency of capsaicin. It is an amide of vanillylamine and ricinoleic acid, with the hydroxyl group on ricinoleic acid esterified with phenylacetic acid. It is used to study the function of the TRPV1 receptor and its downstream actions, and has also shown anti-cancer effects in vitro.^[1]^[2]^[3]

References

^ Appendino G, De Petrocellis L, Trevisani M, Minassi A, Daddario N, Moriello AS, et al. (February 2005). "Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential". The Journal of Pharmacology and Experimental Therapeutics. 312 (2): 561–70. doi:10.1124/jpet.104.074864. PMID 15356216. S2CID 816699.
^ Luviano A, Aguiñiga-Sánchez I, Demare P, Tiburcio R, Ledesma-Martínez E, Santiago-Osorio E, Regla I (May 2014). "Antineoplastic activity of rinvanil and phenylacetylrinvanil in leukaemia cell lines". Oncology Letters. 7 (5): 1651–1656. doi:10.3892/ol.2014.1958. PMC 3997731. PMID 24765194.
^ Sánchez-Sánchez L, Alvarado-Sansininea JJ, Escobar ML, López-Muñoz H, Hernández-Vázquez JM, Monsalvo-Montiel I, et al. (July 2015). "Evaluation of the antitumour activity of Rinvanil and Phenylacetylrinvanil on the cervical cancer tumour cell lines HeLa, CaSKi and ViBo". European Journal of Pharmacology. 758: 129–36. doi:10.1016/j.ejphar.2015.04.003. PMID 25864613.

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[1] Appendino G, De Petrocellis L, Trevisani M, Minassi A, Daddario N, Moriello AS, et al. (February 2005). "Development of the first ultra-potent "capsaicinoid" agonist at transient receptor potential vanilloid type 1 (TRPV1) channels and its therapeutic potential". The Journal of Pharmacology and Experimental Therapeutics. 312 (2): 561–70. doi:10.1124/jpet.104.074864. PMID 15356216. S2CID 816699.

[2] Luviano A, Aguiñiga-Sánchez I, Demare P, Tiburcio R, Ledesma-Martínez E, Santiago-Osorio E, Regla I (May 2014). "Antineoplastic activity of rinvanil and phenylacetylrinvanil in leukaemia cell lines". Oncology Letters. 7 (5): 1651–1656. doi:10.3892/ol.2014.1958. PMC 3997731. PMID 24765194.

[3] Sánchez-Sánchez L, Alvarado-Sansininea JJ, Escobar ML, López-Muñoz H, Hernández-Vázquez JM, Monsalvo-Montiel I, et al. (July 2015). "Evaluation of the antitumour activity of Rinvanil and Phenylacetylrinvanil on the cervical cancer tumour cell lines HeLa, CaSKi and ViBo". European Journal of Pharmacology. 758: 129–36. doi:10.1016/j.ejphar.2015.04.003. PMID 25864613.

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Identifiers

IUPAC name [(Z,7R)-18-[(4-Hydroxy-3-methoxyphenyl)methylamino]-18-oxooctadec-9-en-7-yl] 2-phenylacetate
CAS Number	849343-53-9
PubChem CID	25171466
ChemSpider	74098843
Chemical and physical data
Formula	C₃₄H₄₉NO₅
Molar mass	551.768 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCC[C@H](C/C=C\CCCCCCCC(=O)NCC1=CC(=C(C=C1)O)OC)OC(=O)CC2=CC=CC=C2
InChI InChI=1S/C34H49NO5/c1-3-4-5-15-20-30(40-34(38)26-28-18-13-12-14-19-28)21-16-10-8-6-7-9-11-17-22-33(37)35-27-29-23-24-31(36)32(25-29)39-2/h10,12-14,16,18-19,23-25,30,36H,3-9,11,15,17,20-22,26-27H2,1-2H3,(H,35,37)/b16-10-/t30-/m1/s1 Key:LXLBUUJANYSIKU-DJVRBGHSSA-N