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Bremazocine

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Group of stereoisomers

Pharmaceutical compound

Bremazocine
Clinical data


Routes of administration	Oral
ATC code	none
Identifiers
IUPAC name 6-ethyl- 3-[(1-hydroxycyclopropyl)methyl]- 11,11-dimethyl- 1,2,3,4,5,6-hexahydro- 2,6-methano- 3-benzazocin-8- ol or 2-(1-hydroxy- cyclopropylmethyl)- 5-ethyl- 9,9-dimethyl- 2'-hydroxy- 6,7-benzomorphan
CAS Number	83829-76-9^Y
PubChemCID	1223
IUPHAR/BPS	1603
ChemSpider	1186
UNII	ISF76M2DBE
ChEMBL	ChEMBL1797687
CompTox Dashboard(EPA)	DTXSID50868536
Chemical and physical data
Formula	C₂₀H₂₉NO₂
Molar mass	315.457 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES OC1(CC1)CN4[C@@H]3Cc2c(cc(O)cc2)[C@@](C3(C)C)(CC4)CC

Bremazocine is aκ-opioid receptor agonist related topentazocine. It haspotent and long-lastinganalgesic anddiuretic effects.^[1] It has 200 times the activity ofmorphine, but appears to have no addictive properties and does not depress breathing.^[2] The crystal structure of bremazocine was determined in 1984^[3]

References

[edit]

^Dortch-Carnes J, Potter DE (2005)."Bremazocine: a kappa-opioid agonist with potent analgesic and other pharmacologic properties".CNS Drug Reviews.11 (2):195–212.doi:10.1111/j.1527-3458.2005.tb00270.x.PMC 6741727.PMID 16007240.
^Patrick G (2013).An Introduction to Medicinal Chemistry (5th expanded ed.). Oxford University Press. p. 641.ISBN 978-0199697397.
^Verlinde CL, Blaton NM, De Ranter CJ, Peeters OM (1984). "5-Ethyl-2'-hydroxy-2-[(1-hydroxycyclopropyl) methyl]-9, 9-dimethyl-6, 7-benzomorphan hydrochloride (bremazocine), C20H29NO2. HCl".Acta Crystallogr. C.40 (10):1759–1761.Bibcode:1984AcCrC..40.1759V.doi:10.1107/S0108270184009434.

Analgesics (N02A,N02B)

Opioids

Opiates/opium	Codeine^# +aspirin +paracetamol Morphine^# (+naltrexone) Opium Laudanum Paregoric
Semisynthetic	Acetyldihydrocodeine Benzylmorphine Buprenorphine (+naloxone) Butorphanol Desomorphine Dihydrocodeine (+paracetamol) Dihydromorphine Etorphine Ethylmorphine Hydrocodone (+paracetamol,+ibuprofen,+aspirin) Hydromorphinol Hydromorphone Levorphanol Metopon Nalbuphine Nicocodeine Nicodicodine Nicomorphine Oxycodone (+paracetamol,+aspirin,+ibuprofen,+naloxone,+naltrexone) Oxymorphone Papaveretum Thebacon
Synthetic	Alfentanil Alphaprodine Anileridine Bezitramide Carfentanil Dextromoramide Dextropropoxyphene Dezocine Dimenoxadol Dipipanone Ethoheptazine Fentanyl^# (+fluanisone) Ketobemidone Lofentanil Meptazinol Methadone^# NFEPP Norpipanone Oliceridine Pentazocine Pethidine (meperidine) Phenadoxone Phenazocine Phenoperidine Piminodine Piritramide Proheptazine Propiram Remifentanil Sufentanil Tapentadol Tegileridine Tilidine Tramadol (+celecoxib,+paracetamol) Viminol

Paracetamol-type

NSAIDs

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Oxicams	Isoxicam Lornoxicam Meloxicam Piroxicam Tenoxicam
Acetates	Acemetacin Bromfenac Diclofenac Etodolac Indometacin (Indometacin farnesil) Ketorolac Sulindac Tolmetin Zomepirac^‡
COX-2 inhibitors	Celecoxib (+tramadol) Etoricoxib Lumiracoxib^‡ Parecoxib Rofecoxib^‡ Valdecoxib^‡
Fenamates	Flufenamic acid Meclofenamic acid Mefenamic acid Tolfenamic acid
Salicylates	Aspirin (acetylsalicylic acid)^# (+paracetamol/caffeine) Aloxiprin Benorylate Carbasalate calcium Choline salicylate Diflunisal Dipyrocetyl Ethenzamide Guacetisal Imidazole salicylate Magnesium salicylate Morpholine salicylate Potassium salicylate Salicin Salicylamide Salsalate Sodium salicylate Wintergreen (methyl salicylate)
Pyrazolones	Aminophenazone^‡ Ampyrone Metamizole (dipyrone) Nifenazone Phenazone Propyphenazone (+paracetamol/caffeine)
Others	Benzydamine Floctafenine Glafenine Nabumetone Nimesulide Proquazone

Cannabinoids

Ion channel
modulators

Calcium blockers	Alcohol (ethanol) Gabapentin Gabapentin enacarbil Leconotide Mirogabalin Pregabalin Ziconotide
Sodium blockers	Carbamazepine Lacosamide Local anesthetics (e.g.,cocaine,lidocaine) Mexiletine Nefopam Tricyclic antidepressants (e.g.,amitriptyline^#) Na_v1.7/1.8-selective:DSP-2230^§ Funapide^§ PF-05089771^§ Suzetrigine
Potassium openers	Flupirtine^‡

Myorelaxants

Others

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

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