(1R,9S,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol

Base Information

• Chemical Name: (1R,9S,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol
• CAS No.: 42408-82-2
• Molecular Formula: C21H29NO2
• Molecular Weight: 327.467
• Hs Code.: 2933499030
• Nikkaji Number: J16.487I
• Mol file: 42408-82-2.mol

Synonyms:DB00611

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Chemical Property of (1R,9S,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol

Chemical Property:

• Melting Point: 215-217°
• Refractive Index: 1.642
• Boiling Point: 507.3 °C at 760 mmHg
• PKA: pKa 8.6 (Uncertain)
• Flash Point: 265.9 °C
• PSA: 43.70000
• Density: 1.24 g/cm³
• LogP: 3.30350
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 327.219829168
• Heavy Atom Count: 24
• Complexity: 492

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC2(C3CC4=C(C2(C1)CCN3CC5CCC5)C=C(C=C4)O)O
• Isomeric SMILES: C1CC[C@]2([C@@H]3CC4=C([C@@]2(C1)CCN3CC5CCC5)C=C(C=C4)O)O
• Uses: Mixed opioid agonist-antagonist. Analgesic (narcotic); antitussive. Controlled substance.
• Therapeutic Function: Analgesic, Antitussive
• Biological Functions: Butorphanol (Stadol) is chemically related to levorphanol but pharmacologically similar in action to pentazocine. As an opioid antagonist it is nearly 30 times as potent as pentazocine and has one-fortieth the potency of naloxone. It is a potent opioid analgesic indicated for the relief of moderate to severe pain. Its potency is 7 times that of morphine and 20 times that of pentazocine as an analgesic. Its onset of action is similar to that of morphine.The side effects and signs of toxicity are similar to those produced by pentazocine. It produces excitatory effects and sedation and precipitates withdrawal in opioid-dependent patients. Although generally administered parenterally because of its low bioavailability following oral administration, it is also unique in that a nasal spray formulation is available.The nasal spray is indicated for the relief of postoperative pain and migraine headache. The low molecular weight of butorphanol, its high lipophilicity, and its lack of vasoconstrictor effects make it particularly suitable for nasal administration.Nasal administration of butorphanol decreases the onset of action to 15 minutes and decreases the firstpass effect of the drug, which increases bioavailability. Generally the patient sprays a set dose of 1 mg per hour for 2 hours. The duration of action is 4 to 5 hours. The convenience of such administration is a major advantage to patients requiring repeat dosing. The abuse potential following such administration has not been extensively studied, although it is thought to be small. Butorphanol is not a federally controlled (“scheduled”) drug, so physicians are not required to obtain the licenses and security safeguards required for other opioid analgesics. Adverse effects, contraindications, and drug interactions are similar to those for pentazocine and morphine.

Technology Process of (1R,9S,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol

There total 9 articles about (1R,9S,10S)-17-(cyclobutylmethyl)-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene-4,10-diol 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: 59.0%

N-Cyclobutylmethyl-14β-hydroxy-3-methoxymorphinan → Butorphanol (42408-82-2)

Guidance literature:

With boron tribromide; In dichloromethane; at 0 - 30 ℃; for 3.5h;

Reference yield: 30.5%

(S)-2-cyclobutylmethyl-1-(4-methoxybenzyl)octahydroisoquinoline-4a,8a-diol → Butorphanol (42408-82-2)

Guidance literature:

(S)-2-cyclobutylmethyl-1-(4-methoxybenzyl)octahydroisoquinoline-4a,8a-diol; With borane-THF; at 25 - 30 ℃; for 0.5h;

With phosphoric acid; at 40 - 45 ℃; for 16h;

With boron tribromide; In dichloromethane; at 0 - 30 ℃; for 3h;

Reference yield:

N-cyclobutylcarbonyl-14-hydroxy-3-methoxymorphinan → Butorphanol (42408-82-2)

Guidance literature:

Multi-step reaction with 2 steps

1: tetrahydrofuran

2: hydrogenchloride; hydrogen bromide

With hydrogenchloride; hydrogen bromide; In tetrahydrofuran;

upstream raw materials:

14β-Hydroxy-3-methoxymorphinan

Downstream raw materials:

benzyl (14-hydroxy-17-cyclobutylmethyl)morphinan-3-yl decanedioate

MCL-693

C₂₉H₃₇NO₂

butorphanol tartrate

Refernces

• 1、 -. "Combination of selected opioids with muscarine antagonists for treating urinary incontinence". . . Retrieved 2008/06/13.
• 2、 -. "Process for the preparation of 14-hydroxymorphinans". . . Retrieved 2008/06/13.