BDPC
Encyclopedia
4--4-(dimethylamino)-1-(2-phenylethyl)cyclohexanol (BDPC, Bromadol) is a potent narcotic
analgesic
with a distinctive chemical structure
. It was developed by Daniel Lednicer at Upjohn in the 1970s. Initial studies showed that it was around 10,000 times the strength of morphine
in animal models although later studies assigned a value of x504 morphine for the trans (the more active) isomer.
, euphoria
, constipation
, itching and respiratory depression which could be harmful or fatal. Tolerance and dependence
would be expected to develop rapidly based on the potency of the drug, as it is of a similar strength to carfentanil
and so would most likely cause pronounced tachyphylaxis
following repeated dosing, as is seen with the potent fentanyl analogues.
is an idea that has been pursued. 2-Hydroxy-PCP and 2-methoxyphencyclidine were both recently reported. The 4-positional isomers would seem like a logical extension of this work. However, it is more common for the 4-keto group to be kept in the form of its corresponding ethylene ketal.
Grünenthal
Ex 6
Narcotic
The term narcotic originally referred medically to any psychoactive compound with any sleep-inducing properties. In the United States of America it has since become associated with opioids, commonly morphine and heroin and their derivatives, such as hydrocodone. The term is, today, imprecisely...
analgesic
Analgesic
An analgesic is any member of the group of drugs used to relieve pain . The word analgesic derives from Greek an- and algos ....
with a distinctive chemical structure
Chemical structure
A chemical structure includes molecular geometry, electronic structure and crystal structure of molecules. Molecular geometry refers to the spatial arrangement of atoms in a molecule and the chemical bonds that hold the atoms together. Molecular geometry can range from the very simple, such as...
. It was developed by Daniel Lednicer at Upjohn in the 1970s. Initial studies showed that it was around 10,000 times the strength of morphine
Morphine
Morphine is a potent opiate analgesic medication and is considered to be the prototypical opioid. It was first isolated in 1804 by Friedrich Sertürner, first distributed by same in 1817, and first commercially sold by Merck in 1827, which at the time was a single small chemists' shop. It was more...
in animal models although later studies assigned a value of x504 morphine for the trans (the more active) isomer.
Opioid pharmacology
BDPC has never been used in humans, but would be expected to produce effects similar to those of other potent opioid agonists, including strong analgesia, sedationSedation
Sedation is the reduction of irritability or agitation by administration of sedative drugs, generally to facilitate a medical procedure or diagnostic procedure...
, euphoria
Euphoria (emotion)
Euphoria is medically recognized as a mental and emotional condition in which a person experiences intense feelings of well-being, elation, happiness, ecstasy, excitement and joy...
, constipation
Constipation
Constipation refers to bowel movements that are infrequent or hard to pass. Constipation is a common cause of painful defecation...
, itching and respiratory depression which could be harmful or fatal. Tolerance and dependence
Physical dependence
Physical dependence refers to a state resulting from chronic use of a drug that has produced tolerance and where negative physical symptoms of withdrawal result from abrupt discontinuation or dosage reduction...
would be expected to develop rapidly based on the potency of the drug, as it is of a similar strength to carfentanil
Carfentanil
Carfentanil or carfentanyl is an analogue of the popular synthetic opioid analgesic fentanyl, and is one of the most potent opioids known . Carfentanil was first synthesized in 1974 by a team of chemists at Janssen Pharmaceutica which included Paul Janssen...
and so would most likely cause pronounced tachyphylaxis
Tachyphylaxis
Tachyphylaxis is a medical term describing a decrease in the response to a drug due to previous exposure to that drug. Increasing the dose of the drug may be able to restore the original response. In this context tachyphylaxis is a synonym for drug tolerance...
following repeated dosing, as is seen with the potent fentanyl analogues.
Structure-activity relationships
Several related analogues such as the p-methyl and ring-unsubstituted compounds have also been investigated. Bromadol is the lead compound in this series that attracted so much interest in it initially. A large number of analogs have been prepared, and the SAR is very well established. Lednicer constructed Dreiding models to show that the model of bromadol will give an exact overlay on a model of fentanyl.NMDA receptor connection
For example, a positional isomer of ketamineKetamine
Ketamine is a drug used in human and veterinary medicine. Its hydrochloride salt is sold as Ketanest, Ketaset, and Ketalar. Pharmacologically, ketamine is classified as an NMDA receptor antagonist...
is an idea that has been pursued. 2-Hydroxy-PCP and 2-methoxyphencyclidine were both recently reported. The 4-positional isomers would seem like a logical extension of this work. However, it is more common for the 4-keto group to be kept in the form of its corresponding ethylene ketal.
Chemistry
It is made from 1,4-cyclohexadione. Details for this are outlined in Organic Syntheses.Grünenthal
Grünenthal
Grünenthal GmbH is a German pharmaceutical company in Stolberg near Aachen, which holds the patent to Ultram , and its much stronger derivative Nucynta , both used as analgesics with Norepinephrine Reuptake Inhibition...
Ex 6