BDPC

Last updated
BDPC
Bromadol.svg
Bromadol 3D BS.png
Clinical data
ATC code
  • None
Identifiers
  • 4-(4-Bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexan-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
Formula C22H28BrNO
Molar mass 402.376 g·mol−1
3D model (JSmol)
Melting point 208 to 210 °C (406 to 410 °F)
  • CN(C)C1(CCC(CC1)(CCC2=CC=CC=C2)O)C3=CC=C(C=C3)Br
  • InChI=1S/C22H28BrNO/c1-24(2)22(19-8-10-20(23)11-9-19)16-14-21(25,15-17-22)13-12-18-6-4-3-5-7-18/h3-11,25H,12-17H2,1-2H3 Yes check.svgY
  • Key:PRSUTWWKYIVBEU-UHFFFAOYSA-N Yes check.svgY
   (verify)

BDPC (systematic name 4-(4-bromophenyl)-4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol; also known as bromadol) is a potent fully synthetic opioid with a distinctive arylcyclohexylamine chemical structure. It was developed by Daniel Lednicer at Upjohn in the 1970s. [1] Initial studies estimated that it was around 10,000 times the potency of morphine in animal models. [2] However, later studies using more modern techniques assigned a value of 504 times the potency of morphine for the more active trans-isomer. [3] This drug was first seized along with three kilograms of acetylfentanyl in an April 25, 2013 police action in Montreal, Canada, [4] and has reportedly continued to be available on the designer drug market internationally. [5] [6] Analogues where the para-bromine is replaced by chlorine or a methyl group retain similar activity, while the meta-hydroxyl derivative demonstrated robust antagonist activity. [7] [8]

p-methyl analogue of BDPC 4Methyl-bromadol structure.png
p-methyl analogue of BDPC
p-chloro analogue of BDPC. 4Chloro-bromadol structure.png
p-chloro analogue of BDPC.
m-hydroxy analogue of BDPC. 3Hydroxy-bromadol structure.png
m-hydroxy analogue of BDPC.

See also

Related Research Articles

<span class="mw-page-title-main">Ohmefentanyl</span> Opioid analgesic

Ohmefentanyl is an extremely potent opioid analgesic drug which selectively binds to the μ-opioid receptor.

<span class="mw-page-title-main">Dihydroetorphine</span> Opioid analgesic drug

Dihydroetorphine was developed by K. W. Bentley at McFarlan-Smith in the 1960s and is a potent opioid analgesic used mainly in China. It is a derivative of the better-known opioid etorphine, a very potent veterinary painkiller and anesthetic medication used primarily for the sedation of large animals such as elephants, giraffes, and rhinos.

<span class="mw-page-title-main">Oripavine</span> Chemical compound

Oripavine is an opioid and the major metabolite of thebaine. It is the parent compound from which a series of semi-synthetic opioids are derived, which includes the compounds etorphine and buprenorphine. Although its analgesic potency is comparable to morphine, it is not used clinically due to its severe toxicity and low therapeutic index. Due to its use in manufacture of strong opioids, oripavine is a controlled substance in some jurisdictions.

<span class="mw-page-title-main">Allylprodine</span> Opioid analgesic drug

Allylprodine is an opioid analgesic that is an analog of prodine. It was discovered by Hoffman-La Roche in 1957 during research into the related drug pethidine. Derivatives were tested to prove the theory that phenolic and non-phenolic opioids bind at different sites of the opiate receptor.

<span class="mw-page-title-main">7-PET</span> Opioid analgesic drug

7-PET is an opioid analgesic drug that has 300 times the potency of morphine by weight. It was discovered by K.W. Bentley and is related to the more well known oripavine derivative etorphine, which is used as a veterinary painkiller and anesthetic medication for the sedation of large animals such as elephants, giraffes, and rhinos. 7-PET itself has a 3-O-methyl ether which reduces potency, but the 3-OH derivative is around 2200 times more potent than morphine, almost the same potency as etorphine as a μ agonist, and unexpectedly the 3-hydrogen compound is also around the same potency of 2000 times morphine.

<span class="mw-page-title-main">Enadoline</span> Chemical compound

Enadoline is a drug which acts as a highly selective κ-opioid agonist.

<span class="mw-page-title-main">Viminol</span> Opioid analgesic medicine

Viminol is an opioid analgesic developed by a team at the drug company Zambon in the 1960s. Viminol is based on the α-pyrryl-2-aminoethanol structure, unlike any other class of opioids.

<span class="mw-page-title-main">14-Phenylpropoxymetopon</span> Chemical compound

14-Phenylpropoxymetopon (PPOM) is an opioid analogue that is a derivative of metopon which has been substituted with a γ-phenylpropoxy group at the 14-position. PPOM is a highly potent analgesic drug several thousand times stronger than morphine, with an even higher in vivo potency than etorphine. The 14-phenylpropoxy substitution appears to confer potent μ-opioid agonist activity, even when combined with substitutions such as N-cyclopropyl or N-allyl, which normally result in μ-opioid antagonist compounds.

<span class="mw-page-title-main">Azaprocin</span> Opioid analgesic drug

Azaprocin is a drug which is an opioid analgesic with approximately ten times the potency of morphine, and a fast onset and short duration of action. It was discovered in 1963, but has never been marketed.

<span class="mw-page-title-main">HZ-2</span> Chemical compound

HZ-2 is a drug which acts as a highly selective κ-opioid agonist. It is a potent analgesic with around the same potency as morphine, with a long duration of action and high oral bioavailability. Side effects include sedation, nausea and dysphoria as well as diuretic effects.

<span class="mw-page-title-main">Arylcyclohexylamine</span> Class of chemical compounds

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

<i>N</i>-Phenethylnormorphine Chemical compound

N-Phenethylnormorphine is an opioid analgesic drug derived from morphine by replacing the N-methyl group with β-phenethyl. It is around eight to fourteen times more potent than morphine as a result of this modification, in contrast to most other N-substituted derivatives of morphine, which are substantially less active, or act as antagonists. Binding studies have helped to explain the increased potency of N-phenethylnormorphine, showing that the phenethyl group extends out to reach an additional binding point deeper inside the μ-opioid receptor cleft, analogous to the binding of the phenethyl group on fentanyl.

<span class="mw-page-title-main">MT-45</span> Chemical compound

MT-45 (IC-6) is an opioid analgesic drug invented in the 1970s by Dainippon Pharmaceutical Co. It is chemically a 1-substituted-4-(1,2-diphenylethyl) piperazine derivative, which is structurally unrelated to most other opioid drugs. Racemic MT-45 has around 80% the potency of morphine, with almost all opioid activity residing in the (S) enantiomer. It has been used as a lead compound from which a large family of potent opioid drugs have been developed, including full agonists, partial agonists, and antagonists at the three main opioid receptor subtypes. Fluorinated derivatives of MT-45 such as 2F-MT-45 are significantly more potent as μ-opioid receptor agonists, and one of its main metabolites 1,2-diphenylethylpiperazine also blocks NMDA receptors.

<span class="mw-page-title-main">U-47700</span> Opioid analgesic

U-47700, also known as U4, pink heroin, pinky, and pink, is an opioid analgesic drug developed by a team at Upjohn in the 1970s which has around 7.5 times the potency of morphine in animal models.

<span class="mw-page-title-main">Dimethylaminopivalophenone</span> Opioid analgesic drug

Dimethylaminopivalophenone is an opioid analgesic with a potency ½ that of morphine. It was initially discovered by Russian scientists in 1954 and subsequently rediscovered in the US in 1969. Its LD50 in mice is 83 mg/kg. It has never been marketed commercially.

<span class="mw-page-title-main">Isotonitazene</span> Chemical compound

Isotonitazene is a benzimidazole-derived opioid analgesic drug related to etonitazene, which has been sold as a designer drug. It has only around half the potency of etonitazene in animal studies, but it is likely even less potent in humans as was seen with etonitazene. Isotonitazene was fully characterized in November 2019 in a paper where the authors performed a full analytical structure elucidation in addition to determination of the potency at the μ-opioid receptor using a biological functional assay in vitro. While isotonitazene was not compared directly to morphine in this assay, it was found to be around 2.5 times more potent than hydromorphone and slightly more potent than fentanyl.

<span class="mw-page-title-main">Diphenpipenol</span> Chemical compound

Diphenpipenol is an opioid analgesic drug invented in the 1970s by Dainippon Pharmaceutical Co. It is chemically a 1-substituted-4-(1,2-diphenylethyl)piperazine derivative related to compounds such as MT-45 and AD-1211, but diphenpipenol is the most potent compound in the series, with the more active (S) enantiomer being around 105 times the potency of morphine in animal studies. This makes it a similar strength to fentanyl and its analogues, and consequently diphenpipenol can be expected to pose a significant risk of producing life-threatening respiratory depression, as well as other typical opioid side effects such as sedation, itching, nausea and vomiting.

4-Dimethylamino-4-(<i>p</i>-tolyl)cyclohexanone Synthetic opioid

4-Dimethylamino-4-(p-tolyl)cyclohexanone (sometimes known as dimetamine) is a opioid analgesic with an arylcyclohexylamine chemical structure. It was developed by Daniel Lednicer at Upjohn in the 1970s. It has around the same analgesic potency as morphine, with analogues where the para-methyl group is replaced by a halogen being slightly weaker. Derivatives where the ketone group has been reacted with a Grignard reagent to add a phenethyl side chain are several hundred times stronger (as is seen in the compound BDPC).

References

  1. US 4366172,Lednicer, Daniel,"4-Amino-cyclohexanols, their pharmaceutical compositions and methods of use",issued 1982-12-28, assigned to Upjohn Company
  2. Lednicer D, VonVoigtlander PF (October 1979). "4-(p-Bromophenyl)-4-(dimethylamino)-1-phenethylcyclohexanol, an extremely potent representative of a new analgesic series". Journal of Medicinal Chemistry . 22 (10): 1157–8. doi:10.1021/jm00196a001. PMID   513062.
  3. Liu ZH, Jin WQ, Dai QY, Chen XJ, Zhang HP, Chi ZQ (May 2003). "Opioid activity of C8813, a novel and potent opioid analgesic". Life Sciences . 73 (2): 233–41. doi:10.1016/S0024-3205(03)00263-7. PMID   12738037.
  4. "Extremely potent painkiller hits Montreal black market". CBC News. May 13, 2013.
  5. Sharma KK, Hales TG, Rao VJ, NicDaeid N, McKenzie C (January 2019). "The search for the "next" euphoric non-fentanil novel synthetic opioids on the illicit drugs market: current status and horizon scanning". Forensic Toxicology. 37 (1): 1–16. doi:10.1007/s11419-018-0454-5. PMC   6314991 . PMID   30636980.
  6. Vandeputte MM, Cannaert A, Stove CP (November 2020). "In vitro functional characterization of a panel of non-fentanyl opioid new psychoactive substances". Archives of Toxicology . 94 (11): 3819–3830. doi:10.1007/s00204-020-02855-7. hdl: 1854/LU-8687070 . PMID   32734307. S2CID   220881657.
  7. Lednicer D, VonVoigtlander PF, Emmert DE (April 1981). "4-amino-4-arylcyclohexanones and their derivatives: a novel class of analgesics. 2. Modification of the carbonyl function". Journal of Medicinal Chemistry . 24 (4): 404–8. doi:10.1021/jm00136a010. PMID   7265128.
  8. Lednicer D, Von Voigtlander PF, Emmert DE (March 1981). "4-aryl-4-aminocyclohexanones and their derivatives, a novel class of analgesics. 3. m-Hydroxyphenyl derivates". Journal of Medicinal Chemistry . 24 (3): 341–6. doi:10.1021/jm00135a019. PMID   7265120.