Nonivamide
기본 정보
- CAS
2444-46-4- 표준 SMILES
CCCCCCCCC(=O)NCc1ccc(O)c(OC)c1- InChIKey
RGOVYLWUIBMPGK-UHFFFAOYSA-N- 분자식
- C17H27NO3
- 평균 분자량
- 293.4 g/mol
- 단동위원소 질량
- 293.19909372
개요
Nonivamide is 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. It has a role as a lachrymator. It is a member of phenols and a capsaicinoid.
이름 및 식별자
- 우선 이름
- Nonivamide
- IUPAC
- N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
- 영어명
- Nonivamide
- 분자식
- C17H27NO3
- 분자량
- 293.4
이름 및 동의어
NONIVAMIDEN-Vanillylnonanamide2444-46-4PseudocapsaicinPelargonic acid vanillylamideN-VanillylnonamideN-VanillylpelargonamideN-(4-Hydroxy-3-methoxybenzyl)nonanamideNonanoic acid vanillylamideN-Nonanoyl vanillylamideVanillyl pelargonic amideVanillyl-N-nonylamide
이름 더 보기
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
데이터베이스 식별자
- CAS
2444-46-4- PubChem CID
- 2998
- DTXSID
DTXSID1034769- ChEMBL
CHEMBL75124- ChEBI
CHEBI:46936- UNII
- S846B891OR
- EC Number
- 219-484-1
- Nikkaji
- J7.575B
물성
구조 계산 물성
- XLogP
- 4.2
- 극성 표면적
- 58.6 Ų
- 수소 결합 공여자 수
- 2
- 수소 결합 수용자 수
- 3
- 회전 가능 결합 수
- 10
- 무거운 원자 수
- 21
- 형식 전하
- 0
- 복잡도
- 283
실험 및 물리화학적 성질
Chemical ClassesOther Uses -> Food Additives
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amines [FA0802]
CosmeticsMasking
Fragrances
Fragrance Ingredient (Nonanoyl 4-hydroxy-3-methoxybenzylamide) -> IFRA transparency List
Fragrance
LogP2.96
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
Soluble in water (slightly)
slightly
Slightly soluble in water
Soluble (in ethanol)
Human DrugsPharmaceuticals
Melting Point124.00 to 128.00 °C. @ 760.00 mm Hg
Physical Description
Powder with a stinging odor; [Sigma-Aldrich MSDS]
Solid
White powder or crystals; odourless
물리화학적 성질
- 녹는점
- 54 °C · 54°C
- 끓는 점
- 200 · 200-210 °C(Press: 0.05 Torr)
- 밀도
- 1 · 1,1 g/cm3
- FEMA
- 2787 · 2787 | NONANOYL 4-HYDROXY-3-METHOXYBENZYLAMIDE
- 인화점
- 190 °C · 190°C
- 저장 조건
- 2 · Sealed in dry,2-8°C
- 용해도
- 100 mg/mL, · 메탄올: 100mg/mL, 투명하거나 약간 흐릿함
- 물리적 상태
- 가루
- 산도 계수 (pKa)
- 9.76 · 9.76±0.20(Predicted)
- 색상
- 흰색에서 황백색까지
- 냄새
- 무취의
- 냄새 유형
- 온화한
- JECFA Number
- 1599 · 1599
- BRN
- 2144300 · 2144300
- 안정성
- 안정적인. 강한 산화제와 호환되지 않습니다.
- 주요 응용
- 청소용품화장품향료 및 향음식 및 음료개인 위생 관리
- 화장품 원료 기능
- 향기
- InChI
- 1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)
- InChIKey
- RGOVYLWUIBMPGK-UHFFFAOYSA-N
- SMILES
- CCCCCCCCC(=O)NCc1ccc(O)c(OC)c1
- LogP
- 3.43 · 3.43
- EPA
- Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]- (2444-46-4)
화학적 성질
solid
안전 및 규제
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
GHS 분류
GHS Classification
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]
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.
유해성 정보
Regulatory Information
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
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%)
안전 데이터
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- RA5998000
- ridadr
- UN 3462 6.1/PG 2
- 독성
- mouse,LD50,intraperitoneal,8mg/kg (8mg/kg),Journal of Medicinal Chemistry. Vol. 36, Pg. 2595, 1993.
- HS 번호
- 29242990
- risk_code
- 25-36/37/38-43
- hazard_code
- T,Xi
- safety_code
- 26-45-37/39-36/37
- 포장분류
- II
- 위험 등급
- 6.1
- 기존화학 물질
- KE-20626
- F 고인화성물질
- 19
- Hazard Classifications
- Eye Dam. 1Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
PharmacodynamicsRelieves minor aches and pains of muscles and joints,.
Mechanism of Action
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
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
용도 및 제조
Uses
Used as a flavoring agent; [FDA]
Use (kg; approx.) in Germany (2009): >50
Use Classification
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
응용 분야
개요Nonanoyl-4-hydroxy-3-methoxybenzylamide is odorless with a pungent, burning taste. Synthesized from nonanyl chloride and vanillylamine.
용도analgesic (topical), depletes Substance P
제조 방법
From nonanyl chloride and vanillylamine.
상·하류 제품 정보
상류 원료
하류 제품
추가 설명
정의ChEBI: 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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