Buprenorphine

Base Information

• Chemical Name: Buprenorphine
• CAS No.: 52485-79-7
• Molecular Formula: C29H41 N O4
• Molecular Weight: 467.649
• European Community (EC) Number: 257-950-6
• UNII: 40D3SCR4GZ
• DSSTox Substance ID: DTXSID2022705
• Wikipedia: Buprenorphine
• Wikidata: Q407721
• NCI Thesaurus Code: C61656
• RXCUI: 1819
• Pharos Ligand ID: 1MYL2TZ39DL2
• Metabolomics Workbench ID: 43188
• ChEMBL ID: CHEMBL560511
• Mol file: 52485-79-7.mol

Synonyms:6029 M;6029-M;6029M;Buprenex;Buprenorphine;Buprenorphine Hydrochloride;Buprex;Hydrochloride, Buprenorphine;Prefin;RX 6029 M;RX-6029-M;RX6029M;Subutex;Temgésic;Temgesic

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Buprenorphine

Chemical Property:

• Melting Point: 260-262°C
• Refractive Index: 1.6290 (estimate)
• Boiling Point: °Cat760mmHg
• PKA: pKa 8.24(H2O t=23.0±0.3) (Uncertain)
• Flash Point: °C
• PSA: 62.16000
• Density: 1.26g/cm³
• LogP: 5.15370
• Storage Temp.: ?20°C
• Solubility.: Very slightly soluble in water, freely soluble in acetone, soluble in methanol, slightly soluble in cyclohexane. It dissolves in dilute solutions of acids.
• XLogP3: 5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 467.30355879
• Heavy Atom Count: 34
• Complexity: 869

Purity/Quality:

Safty Information:

• Pictogram(s): F,T
• Hazard Codes: F,T
• Statements: 11-23/24/25-39/23/24/25
• Safety Statements: 16-36/37-45-7

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Substance Abuse Treatment Agents
• Canonical SMILES: CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O
• Isomeric SMILES: C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)(C(C)(C)C)O
• Recent ClinicalTrials: Emergency Department-Initiated Buprenorphine Validation Network Trial
• Recent EU Clinical Trials: Multicentre, randomized, open-label study to prove an additional
• Recent NIPH Clinical Trials: Phase II Clinical Study of BTDS in Japanese Patients with Cancer Pain
• Uses: Controllled substance (narcotic). Analgesic that demonstrates narcotic agonist-antagonist properties.
• Biological Functions: Buprenorphine (Temgesic) is a mixed agonist–antagonist and a derivative of the naturally occurring opioid thebaine. Buprenorphine is highly lipophilic and is 25 to 50 times more potent than morphine as an analgesic. The sedation and respiratory depression it causes are more intense and longer lasting than those produced by morphine. Its respiratory depressant effects are not readily reversed by naloxone. It binds to the -receptor with high affinity and only slowly dissociates from the receptor, which may explain the lack of naloxone reversal of respiratory depression. Buprenorphine has more agonist than antagonist effects and is often considered a partial agonist rather than a mixed agonist–antagonist, although it precipitates withdrawal in opioid-dependent patients. Its pharmacological effects are similar to those produced by both morphine and pentazocine. Indications for its use are similar to those of pentazocine, that is, for moderate to severe pain. Sublingual preparations are available, but have a slow onset and erratic absorption. The abuse potential of buprenorphine is low.While high doses of the drug are perceived by addicts as being morphinelike, it does reduce the craving for morphine and for the stimulant cocaine. Thus, buprenorphine is a potential new therapy for the treatment of addiction to both classes of drugs. Drug interactions and contraindications are similar to those described for pentazocine and morphine.
• Clinical Use: Opioid analgesic
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: possible opiate withdrawal with other opioids. Antidepressants: possible CNS excitation or depression (hypotension or hypertension) if administered with MAOIs or moclobemide - avoid; sedative effects possibly increased when given with tricyclics. Antifungals: metabolism inhibited by ketoconazole - reduce buprenorphine dose. Antihistamines: sedative effects possibly increased with sedating antihistamines. Antipsychotics: enhanced hypotensive and sedative effects. Antivirals: concentration possibly increased by ritonavir; possibly reduced tipranavir concentration. Dopaminergics: avoid with selegiline. Sodium oxybate: avoid concomitant use.

Technology Process of Buprenorphine

There total 96 articles about Buprenorphine 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: 98.0%

17-cyclopropylmethyl-4,5α-epoxy-6α,14α-etheno-7α-(1-hydroxy-1,2,2-trimethylpropyl)-6β-methoxymorphinan-3-ol → Buprenorphine (52485-79-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In water; isopropyl alcohol; at 80 ℃; for 16h; under 760.051 Torr; Reagent/catalyst;

Reference yield: 98.0%

buprenorphine acetate tetrahydrate → Buprenorphine (52485-79-7)

Guidance literature:

In n-heptane; at 86 - 99 ℃; for 3.5h; Reagent/catalyst; Temperature; Time; Dean-Stark;

Reference yield: 91.0%

[5α,7α(S)]-17-(cyclopropylmethyl)-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α-methyl-6,14-ethenomorphinan-7-methanol (16524-65-5,22152-10-9,136232-89-8) → Buprenorphine (52485-79-7)

Guidance literature:

With n-pentanethiol; potassium tert-butylate; In N,N-dimethyl-formamide; at 100 - 130 ℃; for 18h; Reagent/catalyst; Solvent; Inert atmosphere; Industrial scale; Green chemistry;

upstream raw materials:

[5α,7α(S)]-17-(cyclopropylmethyl)-α-(1,1-dimethylethyl)-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-α-methyl-6,14-ethenomorphinan-7-methanol

northebaine

N-demethyl-N-formylthebaibe

(5R,6R,7S,9R,13S,14S)-7-Acetyl-4,5-epoxy-18,19-dihydro-3,6-dimethoxy-6,14-ethanomorphinan

Downstream raw materials:

(R,S)-2-ethylidene-1,5-dimethyl-3,3-diphenylpyrrolidine

buprenorphine hydrochloride

3-O-trityl-6-O-desmethyl-buprenorphine

buprenorphine-(2-methoxy-PABA) benzyl ester carbamate

Refernces

• 1、 -. "PROCESS FOR THE SYNTHESIS OF BUPRENORPHINE". Page/Page column 20. . Retrieved 2021/08/06.
• 2、 -. "DEUTERATED COMPOUND AND MEDICAL USE THEREOF". . . Retrieved 2020/01/12.