Palvanil

Modify Date: 2024-01-10 17:38:55

Palvanil Structure
Palvanil structure
Common Name Palvanil
CAS Number 69693-13-6 Molecular Weight 391.58700
Density N/A Boiling Point N/A
Molecular Formula C24H41NO3 Melting Point N/A
MSDS N/A Flash Point N/A

 Use of Palvanil


Palvanil is a capsaicin analogue, shows strong desensitizing capability against the TRPV1 receptor. Palvanil shows anti-nociceptive and anti-inflammation effects[1][2].

 Names

Name N-[(4-hydroxy-3-methoxyphenyl)methyl]hexadecanamide
Synonym More Synonyms

 Palvanil Biological Activity

Description Palvanil is a capsaicin analogue, shows strong desensitizing capability against the TRPV1 receptor. Palvanil shows anti-nociceptive and anti-inflammation effects[1][2].
Related Catalog
In Vitro Palvanil (0.1-1000 nM; 0-300 min) leads to calcium increasment in intracellular[1]. Cell Viability Assay[1] Cell Line: HEK-293 cells Concentration: 0.1, 0.5, 1, 5, 10, 50, 100 and 1000 nM Incubation Time: 0-300 min Result: Produced a dose-dependent increase in intracellular calcium with a EC50 of 0.65 nM.
In Vivo Palvanil (Subcutaneous injection; 1 or 10 mg/kg; once) treatment shows hypothermic effect[2]. Palvanil (Intraperitoneal injection; 100 μL (15 nM) per mouse; once) treatment reduces capsaicin-induced bronchoconstriction[2]. Palvanil (Intravenous injection; 0.5, 0.75, and 1 mg/kg; once) treatment shows antinociceptive effects on formalin-induced nocifensive behavior[2]. Palvanil (Intravenous injection; 0.5, 0.75, and 1 mg/kg; once) treatment inhibits carrageenan-induced inflammation[2]. Palvanil (Intravenous injection; 0.5 and 1 mg/kg; once daily; 7 days) reduces mechanical allodynia and thermal hyperalgesia in SNI mice[2]. Animal Model: Male CD-1 mice[2] Dosage: 1 or 10 mg/kg Administration: Subcutaneous injection; 1 or 10 mg/kg; once Result: Led to a slight and short lasting hypothermic effect, produced late hyperthermia. Animal Model: Female BALB/C mice[2] Dosage: 100 μL (15 nM) per mouse Administration: Intraperitoneal injection; 100 μL (15 nM) per mouse; once Result: Induced a significantly lower bronchoconstriction (from 0.47 to 0.605 cm H2O/L/s). Animal Model: Male CD-1 mice received formalin[2] Dosage: 0.5, 0.75, and 1 mg/kg Administration: Intravenous injection; 0.5, 0.75, and 1 mg/kg; once Result: Reduced the second phase of formalin-induced nociceptive behaviour in a dose-dependent manner. Animal Model: Male C57BL/6J mice with acute inflammation induced by carrageenan[2] Dosage: 2.5 mg/kg Administration: Intravenous injection; 2.5 mg/kg; once Result: Reduced the volume of the oedema in the ipsilateral hind paw (64%). Animal Model: Male CD-1 mice[2] Dosage: 0.5 and 1 mg/kg Administration: Intravenous injection; 0.5 and 1 mg/kg; once daily; 7 days Result: Reduced mechanical allodynia and thermal hyperalgesia at 3 and 7 days after nerve injury in a dose-dependent manner.
References

[1]. Luciano De Petrocellis, et al. N-palmitoyl-vanillamide (palvanil) is a non-pungent analogue of capsaicin with stronger desensitizing capability against the TRPV1 receptor and anti-hyperalgesic activity. Pharmacol Res. 2011 Apr;63(4):294-9.

[2]. Livio Luongo, et al. Palvanil, a non-pungent capsaicin analogue, inhibits inflammatory and neuropathic pain with little effects on bronchopulmonary function and body temperature. Pharmacol Res. 2012 Sep;66(3):243-50.

 Chemical & Physical Properties

Molecular Formula C24H41NO3
Molecular Weight 391.58700
Exact Mass 391.30900
PSA 62.05000
LogP 7.33860

 Synthetic Route

~%

Palvanil Structure

Palvanil

CAS#:69693-13-6

Literature: Dang, Hung The; Kang, Gyeoung Jin; Yoo, Eun Sook; Hong, Jongki; Choi, Jae Sue; Kim, Hyung Sik; Chung, Hae Young; Jung, Jee H. Bioorganic and Medicinal Chemistry, 2011 , vol. 19, # 4 p. 1520 - 1527

~94%

Palvanil Structure

Palvanil

CAS#:69693-13-6

Literature: Wang, Bo; Yang, Fan; Shan, Yi-Fan; Qiu, Wen-Wei; Tang, Jie Tetrahedron, 2009 , vol. 65, # 27 p. 5409 - 5412

~13%

Palvanil Structure

Palvanil

CAS#:69693-13-6

Literature: Kobata, Kenji; Yoshikawa, Koichi; Kohashi, Masahiro; Watanabe, Tatsuo Tetrahedron Letters, 1996 , vol. 37, # 16 p. 2789 - 2790

~%

Palvanil Structure

Palvanil

CAS#:69693-13-6

Literature: Kobata, Kenji; Yoshikawa, Koichi; Kohashi, Masahiro; Watanabe, Tatsuo Tetrahedron Letters, 1996 , vol. 37, # 16 p. 2789 - 2790

~%

Palvanil Structure

Palvanil

CAS#:69693-13-6

Literature: Kobata, Kenji; Yoshikawa, Koichi; Kohashi, Masahiro; Watanabe, Tatsuo Tetrahedron Letters, 1996 , vol. 37, # 16 p. 2789 - 2790

~%

Palvanil Structure

Palvanil

CAS#:69693-13-6

Literature: Ford-Moore; Phillips Recueil des Travaux Chimiques des Pays-Bas, 1934 , vol. 53, p. 855

~%

Palvanil Structure

Palvanil

CAS#:69693-13-6

Literature: Ott; Zimmermann Justus Liebigs Annalen der Chemie, 1921 , vol. 425, p. 328

~%

Palvanil Structure

Palvanil

CAS#:69693-13-6

Literature: Ott; Zimmermann Justus Liebigs Annalen der Chemie, 1921 , vol. 425, p. 328

 Synonyms

N-vanillyl-palmitamide
N-Vanillyl-palmitinamid
N-vanillyl-hexadecanamide
Palvanil