HU-243

Base Information

• Chemical Name: HU-243
• CAS No.: 140835-14-9
• Molecular Formula: C25H40 O3
• Molecular Weight: 388.591
• UNII: SKGOA1RZCT
• DSSTox Substance ID: DTXSID30161476
• Nikkaji Number: J485.526D
• Wikipedia: HU-243
• Wikidata: Q83029898
• ChEMBL ID: CHEMBL85071
• Mol file: 140835-14-9.mol

Synonyms:11-hydroxy-3-(1',1'-dimethylheptyl)hexahydrocannabinol;11-hydroxy-3-(1',1'-dimethylheptyl)hexahydrocannabinol, (+-)-(6AA,9A,10AB)-stereoisomer;11-hydroxy-3-(1',1'-dimethylheptyl)hexahydrocannabinol, (+-)-(6AA,9B,10AB)-stereoisomer;11-hydroxy-3-(1',1'-dimethylheptyl)hexahydrocannabinol, (6AR-(6AA,9B,10AB))-stereoisomer;11-hydroxy-3-(1',1'-dimethylheptyl)hexahydrocannabinol, (6AS-(6AA,9A,10AB))-stereoisomer;11-hydroxy-3-(1',1'-dimethylheptyl)hexahydrocannabinol, (6AS-(6AA,9B,10AB))-stereoisomer;HDHHC

Chemical Property of HU-243

Chemical Property:

• PSA: 49.69000
• LogP: 6.30340
• XLogP3: 7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 7
• Exact Mass: 388.29774513
• Heavy Atom Count: 28
• Complexity: 500

Purity/Quality:

99% ^*data from raw suppliers

HU-243 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCC(C)(C)C1=CC(=C2C3CC(CCC3C(OC2=C1)(C)C)CO)O
• Isomeric SMILES: CCCCCCC(C)(C)C1=CC(=C2[C@@H]3C[C@@H](CC[C@H]3C(OC2=C1)(C)C)CO)O
• Uses: A synthetic cannabinoid derivative that acts as a potent agonist at both the CB1 and CB2 receptors. Controlled Substance.

Technology Process of HU-243

There total 7 articles about HU-243 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:

dexanabinol (112924-45-5,137428-19-4,112830-95-2) → [3H]-HU 243 (140835-14-9) + (6aR,9S,10aR)-3-(1,1-Dimethyl-heptyl)-9-hydroxymethyl-6,6-dimethyl-6a,7,8,9,10,10a-hexahydro-6H-benzo[c]chromen-1-ol

Guidance literature:

With (S,S)-2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis(diphenylphosphino)butane; tris(phenylphosphine)rhodium(I) chloride; In ethanol; at 140 ℃; for 48h; under 10336 Torr; Yields of byproduct given;

DOI:10.1021/jm00089a018

Reference yield:

nabilone → [3H]-HU 243 (140835-14-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / K₂CO₃, 18-crown-6 / acetone / 5 h / Heating

2: 1.) n-butyllithium / 1.) hexane, Et₂O, -60 deg C, 15 min, 2.) hexane, Et₂O, RT, 48 h

3: aq. conc. HCl / hexane; diethyl ether / 24 h

4: 68 percent / H₂ / Pd/C / ethanol / 5 h / 2068.6 Torr / Ambient temperature

5: 79 percent / lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1 h / 0 °C

With hydrogenchloride; n-butyllithium; lithium tri(t-butoxy)aluminum hydride; 18-crown-6 ether; hydrogen; potassium carbonate; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane; acetone;

DOI:10.1021/jm00042a015

Reference yield:

nabilone benzylate → [3H]-HU 243 (140835-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-butyllithium / 1.) hexane, Et₂O, -60 deg C, 15 min, 2.) hexane, Et₂O, RT, 48 h

2: aq. conc. HCl / hexane; diethyl ether / 24 h

3: 68 percent / H₂ / Pd/C / ethanol / 5 h / 2068.6 Torr / Ambient temperature

4: 79 percent / lithium tri-tert-butoxyaluminohydride / tetrahydrofuran / 1 h / 0 °C

With hydrogenchloride; n-butyllithium; lithium tri(t-butoxy)aluminum hydride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; ethanol; hexane;

DOI:10.1021/jm00042a015

upstream raw materials:

dexanabinol

Refernces

• 1、 Devane, William A.,Breuer, Aviva,Sheskin, Tzviel,Jaerbe, Torbjoern U. C.,Eisen, Moris S.,Mechoulam, Raphael. "A Novel Probe for the Cannabinoid Receptor". . p. 2065 - 2069. Retrieved 1992.