S-2 METHANANDAMIDE

Base Information

• Chemical Name: S-2 METHANANDAMIDE
• CAS No.: 157182-48-4
• Molecular Formula: C₂₃H₃₉NO₂
• Molecular Weight: 361.568
• Mol file: 157182-48-4.mol

Synonyms:5,8,11,14-Eicosatetraenamide,N-(2-hydroxypropyl)-, [S-(all-Z)]-; (S)-N-(2-hydroxypropyl)arachidonylamide; AM355; AM 355 (pharmaceutical)

Chemical Property of S-2 METHANANDAMIDE

Chemical Property:

• Boiling Point: 529.0±50.0 °C(Predicted)
• PKA: 14.55±0.20(Predicted)
• PSA: 49.33000
• Density: 0.935±0.06 g/cm3(Predicted)
• LogP: 6.02000
• Solubility.: ≤10mg/ml in DMSO;10mg/ml in dimethyl formamide

Purity/Quality:

99% ^*data from raw suppliers

S-2 Methanandamide ≥98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: S-2 methanandamide is the second most potent CB1 receptor agonist in the methanandamide series. It has a Ki value of 26 nM for the CB1 receptor. S-2 methanandamide is also less prone to FAAH inactivation and inhibits the murine vas deferens twitch response with an IC50 value of 47 nM.

Technology Process of S-2 METHANANDAMIDE

There total 6 articles about S-2 METHANANDAMIDE 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: 80.0%

ethyl arachidonate (95285-77-1,1808-26-0) + 3-amino-2-propanol (78-96-6,1674-56-2) → N-arachidonoyl(1-amino-2-propanol) (157182-48-4)

Guidance literature:

With Candida antarctica B lipase; Enzymatic reaction;

DOI:10.1002/ejoc.201501263

Reference yield:

all cis 5,8,11,14-eicosatetraenoic acid (506-32-1,236743-58-1) → (+)-2-Methanandamide (157182-48-4)

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) → (-)-2-Methanandamide (157182-48-4)

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

upstream raw materials:

(S)-1-amino-2-propanol

arachidonoyl chloride

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

(2R)-hydroxypropylamine

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 1994.