Nonivamid

Nonivamide

HCID 2998CAS 2444-46-4

Grundinformationen

Standard-SMILES
CCCCCCCCC(=O)NCc1ccc(O)c(OC)c1
InChIKey
RGOVYLWUIBMPGK-UHFFFAOYSA-N
Summenformel
C17H27NO3
Durchschnittliche Molmasse
293,4 g/mol
Monoisotopische Masse
293,19909372

Namen und Bezeichner

Bevorzugter Name
Nonivamide
IUPAC
N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
Lokaler Name
Nonivamid
Englischer Name
Nonivamide
Summenformel
C17H27NO3
Molmasse
293.4

Namen und Synonyme

NONIVAMIDEN-Vanillylnonanamide2444-46-4PseudocapsaicinPelargonic acid vanillylamideN-VanillylnonamideN-VanillylpelargonamideN-(4-Hydroxy-3-methoxybenzyl)nonanamideNonanoic acid vanillylamideN-Nonanoyl vanillylamideVanillyl pelargonic amideVanillyl-N-nonylamide
Weitere Namen anzeigen
SYNTHETIC CAPSAICINCapsaicinoidPAVAcapscaisinNON-4-ENEnonivamide powder
Nonylic acid vanillylamidePelargonyl vanillylamideHydroxymethoxybenzyl pelargonamideN-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamideNonivamidaNonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-Nonanoyl vanillylamideFEMA No. 2787

Datenbank-Bezeichner

CAS
2444-46-4
PubChem CID
2998
DTXSID
DTXSID1034769
ChEMBL
CHEMBL75124
ChEBI
CHEBI:46936
UNII
S846B891OR
EC Number
219-484-1
Nikkaji
J7.575B

Eigenschaften

Berechnete Struktureigenschaften

XLogP
4,2
Polarare Oberfläche (TPSA)
58,6 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
10
Schwere Atome
21

Experimentelle und physikochemische Eigenschaften

Solubility · 4 Einträge

Soluble in water (slightly)

slightly

Slightly soluble in water

Soluble (in ethanol)

Boiling Point492.7
Melting Point · 2 Einträge

57

124.00 to 128.00 °C. @ 760.00 mm Hg

Physical Description · 3 Einträge

Powder with a stinging odor; [Sigma-Aldrich MSDS]

Solid

White powder or crystals; odourless

Dissociation Constants9.77
Collision Cross Section178.0 Ų [M+Na]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID1034769]

Physikochemische Eigenschaften

Schmelzpunkt
54 °C · 54°C
Siedepunkt
200 · 200-210 °C(Press: 0.05 Torr)
Dichte
1 · 1,1 g/cm3
FEMA
2787 · 2787 | NONANOYL 4-HYDROXY-3-METHOXYBENZYLAMIDE
Flammpunkt
190 °C · 190°C
storage temp.
2 · Sealed in dry,2-8°C

Sicherheit und Regulatorisches

GHS-Klassifizierung

GHS Classification · 6 Einträge

This chemical does not meet GHS hazard criteria for 0.3% (5 of 1513) of reports.

Danger

H301 (85.7%): Toxic if swallowed [Danger Acute toxicity, oral];H315 (99.6%): Causes skin irritation [Warning Skin corrosion/irritation];H317 (89.2%): May cause an allergic skin reaction [Warning Sensitization, Skin];H318 (85.7%): Causes serious eye damage [Danger Serious eye damage/eye irritation];H319 (14%): Causes serious eye irritation [Warning Serious eye damage/eye irritation];H334 (85.7%): May cause allergy or asthma symptoms or breathing difficulties if inhaled [Danger Sensitization, respiratory];H335 (14.1%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 1513 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 5 of 1513 reports by companies.;There are 16 notifications provided by 1508 of 1513 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory Information · 3 Einträge

Chemical: Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Nonivamide: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-: Human health tier I assessment
Hazards Summary · 1 Eintrag

Effects sensory neurons; [ChemIDplus] Causes lung inflammation in acute inhalation studies of mice; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; May cause skin sensitization; [Sigma-Aldrich MSDS] Search for (2444-46-4[EC/RN Number]) AND (sensitizer OR sensitization OR dermatitis OR allergic): no results; [PubMed]

Hazard Classes and CategoriesAcute Tox. 3 (85.7%);Skin Irrit. 2 (99.6%);Skin Sens. 1 (89.2%);Eye Dam. 1 (85.7%);Eye Irrit. 2 (14%);Resp. Sens. 1 (85.7%);STOT SE 3 (14.1%)

Regulatorische Informationen

Regulatory Information · 3 Einträge

Chemical: Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Nonivamide: Does not have an individual approval but may be used under an appropriate group standard

Sicherheitsdaten

F
19
wgk
3
tsca
TSCA listed
ridadr
UN 3462 6.1/PG 2
hs_code
29242990
RTECS-Nr.
RA5998000

Chemie und Industrie

Pharmakologische Informationen

PharmacodynamicsRelieves minor aches and pains of muscles and joints,.
Mechanism of Action · 1 Eintrag

Nonivamide is a naturally occurring analog of [DB06774], isolated from peppers, described to produce effects similar to [DB06774]. It is an agonist of the VR1 (vanilloid/TRPV1 receptor). It serves as a transient agonist of these receptors, which are potentiated by pro-inflammatory drugs, a phenomenon that leads to thermal hyperalgesia, or increased heat sensation. Nonivamide has been shown to stimulate afferent neurons with about half the potency of [DB06774]. Agonism of the VR1 (TRPV1) (vanilloid) receptor by Nonivamide was demonstrated to induce the release of Ca2+ from the endoplasmic reticulum (ER) of human lung cells, producing ER stress and cell death [MSDS]. Nonivamide, like other capsaicinoids, acts on the vanilloid receptors located in the peripheral afferent nerve fibers, providing short-acting irritant and algesic properties. Applied dermally, these substances act by stimulating sensitive chemoreceptors of the skin and by reflex, hyperemia and a local elevation in temperature. After repetitive administration, capsaicinoids have been reported to lead to desensitization to nociceptive stimuli possibly by long-acting depletion of peptide neurotransmitters (substance P) from peripheral sensory neurons. Capsaicinoids can modulate muscle tone (in bladder, bronchus etc.). Intravenous injection of nonivamide to rats (10 μg/kg) has been found to lead to bradycardia. The cardiovascular effects are partly explained by substance P release. Nonivamide given to rats subcutaneously (1 mg/kg) was found to cause body temperature decrease, vasodilatation, and increased salivation. Capsaicinoids have shown to illicit bronchospastic effects in guinea pigs. Capsaicin and its analogs were reported to increase barbiturate sleeping time in rats by interacting with hepatic metabolizing enzymes.

Biological Half-LifeAbout 7 minutes.
Metabolism/Metabolites · 1 Eintrag

Limited information is available on pharmacokinetics and metabolism of nonivamide. For the closely related [DB06774] and other capsaicinoids, gastrointestinal absorption is rapid and almost entirely complete in studies of rats (oral dose of about 10 to 15 mg/kg of combined capsaicin and dihydrocapsaicin) with about 85% of the dose being absorbed within 3 hours. Both substances undergo first-pass metabolism in the liver and partly metabolized at the site of absorption.

MeSH Pharmacological ClassificationDrugs that act on neuronal sensory receptors resulting in an increase, decrease, or modification of afferent nerve activity. (From Smith and Reynard, Textbook of Pharmacology, 1991, p367)
Cellular LocationsExtracellular;Membrane

Verwendung und Herstellung

Uses · 2 Einträge

Used as a flavoring agent; [FDA]

Use (kg; approx.) in Germany (2009): >50;Consumption (g per capita; approx.) in Germany (2009): 0.000611;Calculated removal (%): 98.2

Use Classification · 6 Einträge

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Pharmaceuticals

Cosmetics -> Masking

General Manufacturing InformationNonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-: ACTIVE

Anwendungen

BeschreibungNonanoyl-4-hydroxy-3-methoxybenzylamide is odorless with a pungent, burning taste. Synthesized from nonanyl chloride and vanillylamine.

Verwendenanalgesic (topical), depletes Substance P

Darstellung

synthetischeFrom nonanyl chloride and vanillylamine.

Anbieter50 Anbieter

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]
科瑞迪化学400-821-5857 021-64326257 · [email protected]

Ergänzende Hinweise

DefinitionChEBI: A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.

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