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

Base Information

• Chemical Name: N-[(2R)-1-hydroxypropan-2-yl]eicosa-5,8,11,14-tetraenamide
• CAS No.: 157182-49-5
• Molecular Formula: C23H39 N O2
• Molecular Weight: 361.5613
• DSSTox Substance ID: DTXSID70425004
• Wikipedia: Methanandamide
• Wikidata: Q27194429
• Mol file: 157182-49-5.mol

Synonyms:157182-49-5;N-[(2R)-1-hydroxypropan-2-yl]eicosa-5,8,11,14-tetraenamide;R(+)-Methanandamide;CBiol_001724;CBiol_002048;KBioGR_000005;KBioSS_000005;KBio2_000005;KBio2_002573;KBio2_005141;KBio3_000009;KBio3_000010;DTXSID70425004;Bio1_000010;Bio1_000334;Bio1_000499;Bio1_000823;Bio1_000988;Bio1_001312;Bio2_000005;Bio2_000485;N-[(2R)-1-hydroxypropan-2-yl]icosa-5,8,11,14-tetraenamide;PD133429;Q27194429

Chemical Property of N-[(2R)-1-hydroxypropan-2-yl]eicosa-5,8,11,14-tetraenamide

Chemical Property:

• Appearance/Colour: Colorless oil
• Vapor Pressure: 2.11E-13mmHg at 25°C
• Boiling Point: 529 °C at 760 mmHg
• PKA: 14.51±0.10(Predicted)
• Flash Point: 273.8 °C
• PSA: 49.33000
• Density: 0.935 g/cm³
• LogP: 6.02000
• Storage Temp.: −20°C
• Sensitive.: Air & Light Sensitive
• XLogP3: 5.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 16
• Exact Mass: 361.298079487
• Heavy Atom Count: 26
• Complexity: 436

Purity/Quality:

98%,99%, ^*data from raw suppliers

(R)-Methanandamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F
• Hazard Codes: F
• Statements: 11
• Safety Statements: 7-16

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)NC(C)CO
• Isomeric SMILES: CCCCCC=CCC=CCC=CCC=CCCCC(=O)N[C@H](C)CO
• Description: R-1 methanandamide is a potent cannabinoid (CB) receptor 1 agonist in the methanandamide series. It is selective for CB1 over CB2 receptors with Ki values ranging from 17.9 to 28.3 and 815 to 868 nM, respectively. R-1 methanandamide is more potent than arachidonoyl ethanolamide (AEA; ). In addition, R-1 methanandamide is more resistant than AEA to hydrolytic inactivation by fatty acid amide hydrolase (FAAH).

Technology Process of N-[(2R)-1-hydroxypropan-2-yl]eicosa-5,8,11,14-tetraenamide

There total 3 articles about N-[(2R)-1-hydroxypropan-2-yl]eicosa-5,8,11,14-tetraenamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 78.3%

(R)-2-aminopropan-1-ol (35320-23-1) + arachidonoyl chloride (57303-04-5) → methanandamide (157182-49-5,157182-50-8)

Guidance literature:

In dichloromethane; at 0 - 20 ℃; for 1h;

DOI:10.1016/S0928-0987(03)00044-7

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → methanandamide (157182-49-5,157182-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / dimethylformamide; benzene / 1 h / 25 °C

2: tetrahydrofuran; dimethylformamide / 0.25 h / Ambient temperature

With oxalyl dichloride; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm00038a020

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → methanandamide (157182-49-5,157182-50-8)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 2 h / 0 - 20 °C

2: 78.3 percent / CH₂Cl₂ / 1 h / 0 - 20 °C

With oxalyl dichloride; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0928-0987(03)00044-7

upstream raw materials:

(R)-2-aminopropan-1-ol

arachidonoyl chloride

all cis 5,8,11,14-eicosatetraenoic acid

Downstream raw materials:

(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (4-benzoyl-L-phenylalaninate)

(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} 4-benzoyl-N-(5-hexynoyl)-L-phenylalaninate

(+)-{(2R)-2-[(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoylamino]propyl} (2S)-3-(4-benzoylphenyl)-2-[(tert-butoxycarbonyl)amino]propanoate

Refernces

• 1、 Abadji,Lin,Taha,Griffin,Stevenson,Pertwee,Makriyannis. "(R)-methanandamide: A chiral novel anandamide possessing higher potency and metabolic stability". . p. 1889 - 1893. Retrieved 2007/10/02.