(5Z,8Z,11Z,14Z)-N-[(2R)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide

• ChemBase编号: 132563
• 分子式: C23H39NO2
• 平均质量: 361.56126
• 单一同位素质量: 361.29807949
• SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@H](C)CO
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N[C@@H](CO)C
• InChI: InChI=1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-23(26)24-22(2)21-25/h7-8,10-11,13-14,16-17,22,25H,3-6,9,12,15,18-21H2,1-2H3,(H,24,26)/b8-7-,11-10-,14-13-,17-16-/t22-/m1/s1
• InChIKey: SQKRUBZPTNJQEM-FQPARAGTSA-N

名称和登记号

名称

• IUPAC标准名: (5Z,8Z,11Z,14Z)-N-[(2R)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide
• IUPAC传统名: methanandamide
• 别名: AM-356; R(+)-Arachidonyl-1′-hydroxy-2′-propylamide; R(+)-Methanandamide

登记号

• CAS号: 157182-49-5
• EC号: 200-578-6
• MDL号: MFCD00467914
• PubChem SID: 24896698; 162226840
• PubChem CID: 6321351

理论计算性质

• Acid pKa: 15.0486
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): 5.7303762
• LogD (pH = 7.4): 5.730377
• Log P: 5.730377
• 摩尔折射率: 117.384 cm^3
• 极化性: 43.9922 Å^3
• 极化表面积: 49.33 Å^2
• 可自由旋转的化学键: 16
• 里宾斯基五规则: false

分子性质

理化性质

• 闪点: 14 °C; 57.2 °F
• 比旋光度: [α]/D +8.7°, c = 4 in chloroform(lit.)

安全信息

• 保存条件: desiccated; protect from light; under inert gas
• 欧盟危险性物质标志: 易燃性(Flammable) (F)
• 联合国危险货物编号: 1170
• 德国WGK号: 2
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11
• 安全公开号: 7-16
• GHS危险品标识: GHS02
• GHS警示词: Danger
• GHS危险声明: H225
• GHS警示性声明: P210
• 个人保护装置: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1170 3/PG 2
• 毒品管制信息: regulated under CDSA - not available from Sigma-Aldrich Canada
• 保存温度: -20°C

药理学性质

• 相关基因信息: mouse ... Cnr1(12801), Cnr2(12802)rat ... Cnr1(25248)

产品相关信息

• 纯度: ≥96% (HPLC)
• 浓度: 5 mg/mL in absolute ethanol

详细说明

Sigma Aldrich - M186

Biochem/physiol Actions
R(+)-Methanandamide is metabolically stable congener of anandamide that has higher affinity for the cannabinoid receptor. Of the analogs tested, (R)-methanandamide exhibited the highest affinity for the cannabinoid receptor with a Ki of 20 +/- 1.6 nM, 4-fold lower than that of anandamide (Ki = 78 +/- 2 nM). (R)-methanandamide exhibits high stability to aminopeptidase hydrolysis. Experiments with mice have demonstrated that (R)-methanandamide also posseses cannabimimetric properties in vivo, as established by the four tests of hypothermia, hypokinesia, ring immobility, and antinociception.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M186.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.