News and Alerts

VN (Synthetic Capsaicin)

VN (also called PAVA but mistakenly abbreviated as VP) is a chemical that is used in some brands of pepper sprays for use by law enforcement. VN is known by various chemical names such as N-vanillylnonanoamide, Pelargonylvanillylamide, and Nonivamide. The HPLC method (High Pressure Liquid Chromatography) cannot distinguish between VN and Capsaicin. Gas Chromatography and Mass Spectrometer (GC-MS) must be used for proper identification.

Since VN may resemble Capsaicin found naturally in chili peppers, it may lead one to believe that it has the same physiological effects, Scoville Heat Unit, and safety factor as capsaicin widely used in pepper sprays. However, a closer look at scientific data shows that VN differs from Capsaicin. To start with VN's molecular weight is 293.405, whereas Capsaicin's molecular weight is 305.416. Natural Capsaicin derived from chili peppers is therefore heavier than VN and not identical with it.

Toxicity data administered to mouse/hamster via Intraperitoneal route resulted in VN having a lethal dose (LC50) of 8 milligram per each kilogram of body weight (mg/kg) (JMCMAR 36,2595,1993), whereas Capsaicin is greater than >120 (mg/kg) TOXIA6 18,215,1980). This illustrates that very little amount of VN causes greater lethality in laboratory and that Capsaicin is at least 15 times less toxic than VN.

Comprehensive tests and analysis have found the existence of more than 150 pungent compounds that are related to Capsaicin1. Studies have also shown that natural Capsaicin compound known as N-vanillyl-8-methyl-6-nonenamide is more potent than VN. Additionally, VN gave a lower pain and inflammation potency than that of natural Capsaicin.2 Pungency in Scoville Heat Unit of natural and synthetic related compound have also been evaluated (these compound were sampled in their purest form without any impurities) and the following table shows their strength.

In separate studies, Szolcsanyi and Jansco-Gabor synthesized a series of Capsaicin compounds. These synthetic compounds, along with other natural Capsaicin compounds, were then evaluated for their pain-producing potency defined as the concentration in micrograms per milliliter.3 The natural capsaicin compounds showed greater pain production properties than their synthetic counterpart as depicted in the following chart.

Summary: VN is not identical to natural Capsaicin. VN has a higher toxicity level than Capsaicin. VN is less pungent in its SHU level (and therefore not as strong as natural Capsaicin) and lastly VN causes less pain that natural Capsaicin.

References

Newman, A.A., Natural and Synthetic pepper flavored substances (2-6), Chem. Prod. London. 16, 379, 1953: 17, 1954.

Todd, P.H., Jr., Bensinger, M.G., and Bifty, T., Determination of Pungency due to Capsicum by Gas Liquid Chromatography. J. Food Sci., 42. 660. 1977.

Szolcsanyi, J. and Jansco-Gabor, A., Sensory Effects of Capsaicin Congeners. I. Relationship Between Chemical Structure and Pain-Producing Potency of Punget Agents. Arzneim-Forsch. Drug Res., 25. 1877, 1975.

Technical Data

Synonym:

nonivamide
Pelargonsaeure-vanillylamid
pelargonic acid vanillylamide
N-(4-Oxy-3-methoxy-benzyl)-pelargonsaeureamid

CAS: 2444-46-4
Molecular Formula: C17H27NO3
Component Type: isocyclic
Molecular Wt: 293.405
Boiling Pt: 200-210 deg C at 0.05mm

TOXICITY DATA: Intraperitoneal Mouse LD50 8 mg/kg (JMCMAR 36,2595,1993)

Biological Function

Effect on blood pressure and heart rate in normal rats; vagus reflex and heart rate decrease in nonvagotomized rats Antinociceptive activity (mouse and rat hot plate assay, orally, in vivo) and antiinflammatory activity (croton oil-inflamed mouse ear assay, in vivo). Pharmacokinetics, effects on blood pressure, on neurogenic plasma extravasation, chemosensitivity of the eye, depletion of substance P and somatostatin in sciatic nerve and spinal cord at 50 mg/kg s.c. in Sprague-Dawley rats of both sexes blood pressure response (blood pressure, duration, and phase) and untoward vagus reflex hypotensive effect (rats, iv); pungent activity by wiping test (rats); antinociceptive effects on acetic acid-induced writhing in mice (ip, ED50 0.08 mg/kg)

References:

JMCMAR Journal of Medicinal Chemistry. American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037 V.6- 1963-

Janusz, John M., Buckwalter, Brian L., Young, Patricia A., LaHann, Thomas R., Farmer, Ralph W., et al., JMCMAR, J.Med.Chem. ,36 18(1993)2595-2604

Walpole, Christopher S.J., Wrigglesworth, Roger, Bevan, Stuart, Campbell, Elizabeth A., Dray, Andy, et al., JMCMAR, J.Med.Chem., 36 16(1993)2362-2372, 2373-2380, 2381-2389

Chen, Ing-Jun, Yeh, Jwu-Lai, Liou, Shwu-Jen, Shen, Ai-Yu, JMCMAR, J.Med.Chem., 37 7(1994)938-943, 27 3(1992)187-192

Skofitsch, G., Donnerer, J., Lembeck, F., ARZNAD, Arzneim.Forsch.,34 2(1984)154-156

Back to Top