16-methylcyprenorphine profile

## 16-Methylcyprenorphine: A Powerful Tool for Opioid Research

16-Methylcyprenorphine (16-MC) is a **synthetic opioid** with a unique profile that makes it valuable for research. Here's why:

**1. High Affinity for Opioid Receptors:** 16-MC binds very strongly to both **mu (μ)** and **kappa (κ)** opioid receptors, making it an effective **agonist** (activator) at these receptors. This strong binding allows for the study of these receptors and their roles in various physiological processes.

**2. Long-lasting Effects:** Unlike many other opioids, 16-MC has a **prolonged duration of action**, lasting for several hours. This property makes it suitable for investigating the **long-term effects** of opioid receptor activation, as well as for potential applications in drug development for chronic pain management.

**3. Distinct Action Profile:** 16-MC exhibits a **dissociation constant** (Kd) of 0.8 nM at μ receptors and 1.3 nM at κ receptors, indicating a **preference for κ receptors** over μ receptors. This selective action allows researchers to study the unique effects of κ receptor activation, which are often different from those of μ receptors, such as analgesia without the rewarding effects associated with μ agonists.

**4. Potential Applications in Research:** 16-MC is a valuable tool for studying:

* **Opioid receptor function:** Investigating the roles of μ and κ receptors in pain perception, reward pathways, respiratory depression, and other physiological processes.
* **Development of new analgesics:** Exploring the potential of κ agonists for pain relief without addictive properties.
* **Treatment of opioid addiction:** Studying the effects of 16-MC on opioid withdrawal symptoms and relapse prevention.

**5. Advantages over Other Opioids:** 16-MC offers advantages over other opioids, including:

* **Higher selectivity for κ receptors** compared to other κ agonists.
* **Longer duration of action** than many other opioids.
* **Less respiratory depression** than traditional μ agonists.

**Overall, 16-methylcyprenorphine is a powerful tool for studying opioid receptor function and exploring new therapeutic approaches for pain management and opioid addiction.**

**However, it is important to note that 16-MC is still under investigation and its potential clinical applications are still under development.** As with any opioid, further research is needed to fully understand its potential risks and benefits before it can be used safely and effectively in humans.

16-methylcyprenorphine: RN given refers to (5alpha,7alpha,16S)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	162443
SCHEMBL ID	1239514
MeSH ID	M0145807

Synonym
40994-80-7
16-methylcyprenorphine
rx-8008-m
rx 8008m
6,14-ethenomorphinan-7-methanol, 17-(cyclopropylmethyl)-4,5-epoxy-3-hydroxy-6-methoxy-alpha,alpha,16-trimethyl-, (5alpha,7alpha,16s)-
SCHEMBL1239514
(1r,2s,4s,14r,15r,19r)-5-(cyclopropylmethyl)-19-(2-hydroxypropan-2-yl)-15-methoxy-4-methyl-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11,16-tetraen-11-ol
17-(cyclopropylmethyl)-7-(2-hydroxypropan-2-yl)-6-methoxy-16-methyl-4,5-epoxy-6,14-ethenomorphinan-3-ol
DTXSID30961372

Excerpt	Relevance	Reference
" Both antagonists produced large shifts in the dose-response curves to the mu-agonists, morphine and fentanyl, confirming their mu-antagonist activity."	( Reversal by beta-funaltrexamine and 16-methyl cyprenorphine of the antinociceptive effects of opioid agonists in the mouse and guinea-pig. Birch, PJ; Hayes, AG, 1988)	0.27

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	6 (50.00)	18.7374
1990's	6 (50.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	13 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
formaldehyde paraform: polymerized formaldehyde; RN given refers to parent cpd; used in root canal therapy	1.97	1	aldehyde; one-carbon compound	allergen; carcinogenic agent; disinfectant; EC 3.5.1.4 (amidase) inhibitor; environmental contaminant; Escherichia coli metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
fentanyl Fentanyl: A potent narcotic analgesic, abuse of which leads to habituation or addiction. It is primarily a mu-opioid agonist. Fentanyl is also used as an adjunct to general anesthetics, and as an anesthetic for induction and maintenance. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1078). fentanyl : A monocarboxylic acid amide resulting from the formal condensation of the aryl amino group of N-phenyl-1-(2-phenylethyl)piperidin-4-amine with propanoic acid.	1.97	1	anilide; monocarboxylic acid amide; piperidines	adjuvant; anaesthesia adjuvant; anaesthetic; intravenous anaesthetic; mu-opioid receptor agonist; opioid analgesic
ici 204448 ICI 204448: kappa opioid receptor agonist; structure given in first source	1.98	1	monocarboxylic acid
saccharin Saccharin: Flavoring agent and non-nutritive sweetener.. saccharin : A 1,2-benzisothiazole having a keto-group at the 3-position and two oxo substituents at the 1-position. It is used as an artificial sweetening agent.	1.97	1	1,2-benzisothiazole; N-sulfonylcarboxamide	environmental contaminant; sweetening agent; xenobiotic
cyclazocine Cyclazocine: An analgesic with mixed narcotic agonist-antagonist properties.	2.37	2
idazoxan Idazoxan: A benzodioxane-linked imidazole that has alpha-2 adrenoceptor antagonist activity.. idazoxan : A benzodioxine that is 2,3-dihydro-1,4-benzodioxine in which one of the hydrogens at position 2 has been replaced by a 4,5-dihydro-1H-imidazol-2-yl group.	1.98	1	benzodioxine; imidazolines	alpha-adrenergic antagonist
enkephalin, d-penicillamine (2,5)- Enkephalin, D-Penicillamine (2,5)-: A disulfide opioid pentapeptide that selectively binds to the DELTA OPIOID RECEPTOR. It possesses antinociceptive activity.. DPDPE : A heterodetic cyclic peptide that is a cyclic enkephalin analogue, having D-penicillaminyl residues located at positions 2 and 5, which form the heterocycle via a disulfide bond.	1.97	1	heterodetic cyclic peptide	delta-opioid receptor agonist
n,n-diallyl-tyrosyl-alpha-aminoisobutyric acid-phenylalanyl-leucine [no description available]	1.97	1
ethylketocyclazocine Ethylketocyclazocine: A kappa opioid receptor agonist. The compound has analgesic action and shows positive inotropic effects on the electrically stimulated left atrium. It also affects various types of behavior in mammals such as locomotion, rearing, and grooming.	2.37	2
enkephalin, leucine Enkephalin, Leucine: One of the endogenous pentapeptides with morphine-like activity. It differs from MET-ENKEPHALIN in the LEUCINE at position 5. Its first four amino acid sequence is identical to the tetrapeptide sequence at the N-terminal of BETA-ENDORPHIN.. Leu-enkephalin : A pentapeptide comprising L-tyrosine, glycine, glycine, L-phenylalanine and L-leucine residues joined in sequence by peptide linkages. It is an endogenous opioid peptide produced in vertebrate species, including rodents, primates and humans that results from decomposition of proenkephalin or dynorphin and exhibits antinociceptive properties.	2.89	4	pentapeptide; peptide zwitterion	analgesic; delta-opioid receptor agonist; human metabolite; mu-opioid receptor agonist; neurotransmitter; rat metabolite
mr 2266 MR 2266: RN refers to (2R-(2 alpha,6 alpha,11R*))-isomer; structure kappa opioid receptor antagonist	1.97	1
u-50488 3,4-Dichloro-N-methyl-N-(2-(1-pyrrolidinyl)-cyclohexyl)-benzeneacetamide, (trans)-Isomer: A non-peptide, kappa-opioid receptor agonist which has also been found to stimulate the release of adrenocorticotropin (ADRENOCORTICOTROPIC HORMONE) via the release of hypothalamic arginine vasopressin (ARGININE VASOPRESSIN) and CORTICOTROPIN-RELEASING HORMONE. (From J Pharmacol Exp Ther 1997;280(1):416-21). U50488 : A monocarboxylic acid amide obtained by formal condensation between the carboxy group of 3,4-dichlorophenylacetic acid and the secondary amino group of (1R,2R)-N-methyl-2-(pyrrolidin-1-yl)cyclohexanamine	2.66	3	dichlorobenzene; monocarboxylic acid amide; N-alkylpyrrolidine	analgesic; antitussive; calcium channel blocker; diuretic; kappa-opioid receptor agonist
naloxone Naloxone: A specific opiate antagonist that has no agonist activity. It is a competitive antagonist at mu, delta, and kappa opioid receptors.. naloxone : A synthetic morphinane alkaloid that is morphinone in which the enone double bond has been reduced to a single bond, the hydrogen at position 14 has been replaced by a hydroxy group, and the methyl group attached to the nitrogen has been replaced by an allyl group. A specific opioid antagonist, it is used (commonly as its hydrochloride salt) to reverse the effects of opioids, both following their use of opioids during surgery and in cases of known or suspected opioid overdose.	1.98	1	morphinane alkaloid; organic heteropentacyclic compound; tertiary alcohol	antidote to opioid poisoning; central nervous system depressant; mu-opioid receptor antagonist
morphine Meconium: The thick green-to-black mucilaginous material found in the intestines of a full-term fetus. It consists of secretions of the INTESTINAL GLANDS; BILE PIGMENTS; FATTY ACIDS; AMNIOTIC FLUID; and intrauterine debris. It constitutes the first stools passed by a newborn.	1.97	1	morphinane alkaloid; organic heteropentacyclic compound; tertiary amino compound	anaesthetic; drug allergen; environmental contaminant; geroprotector; mu-opioid receptor agonist; opioid analgesic; plant metabolite; vasodilator agent; xenobiotic
beta-funaltrexamine beta-funaltrexamine: RN given refers to parent cpd(E)-isomer; structure given in first source	1.97	1	morphinane alkaloid
naltrexone Naltrexone: Derivative of noroxymorphone that is the N-cyclopropylmethyl congener of NALOXONE. It is a narcotic antagonist that is effective orally, longer lasting and more potent than naloxone, and has been proposed for the treatment of heroin addiction. The FDA has approved naltrexone for the treatment of alcohol dependence.. naltrexone : An organic heteropentacyclic compound that is naloxone substituted in which the allyl group attached to the nitrogen is replaced by a cyclopropylmethyl group. A mu-opioid receptor antagonist, it is used to treat alcohol dependence.	3.48	8	cyclopropanes; morphinane-like compound; organic heteropentacyclic compound	antidote to opioid poisoning; central nervous system depressant; environmental contaminant; mu-opioid receptor antagonist; xenobiotic
norbinaltorphimine norbinaltorphimine: kappa opiate receptor antagonist; structure given in first source	2.67	3	isoquinolines
enkephalin, ala(2)-mephe(4)-gly(5)- Enkephalin, Ala(2)-MePhe(4)-Gly(5)-: An enkephalin analog that selectively binds to the MU OPIOID RECEPTOR. It is used as a model for drug permeability experiments.	2.38	2
chlornaltrexamine chlornaltrexamine: RN given refers to (5alpha,6beta)-isomer	2.37	2
naltrindole naltrindole: delta opioid receptor antagonist	2.38	2	isoquinolines
morphinans Morphinans: Compounds based on a partially saturated iminoethanophenanthrene, which can be described as ethylimino-bridged benzo-decahydronaphthalenes. They include some of the OPIOIDS found in PAPAVER that are used as ANALGESICS.	3.84	12	isoquinoline alkaloid fundamental parent; morphinane alkaloid
enkephalin, leucine-2-alanine Enkephalin, Leucine-2-Alanine: A delta-selective opioid (ANALGESICS, OPIOID). It can cause transient depression of mean arterial blood pressure and heart rate.	1.98	1

Condition	Relationship Strength	Studies
Arrhythmia [description not available]	1.98	1
Coronary Heart Disease [description not available]	2.38	2
Arrhythmias, Cardiac Any disturbances of the normal rhythmic beating of the heart or MYOCARDIAL CONTRACTION. Cardiac arrhythmias can be classified by the abnormalities in HEART RATE, disorders of electrical impulse generation, or impulse conduction.	1.98	1
Coronary Disease An imbalance between myocardial functional requirements and the capacity of the CORONARY VESSELS to supply sufficient blood flow. It is a form of MYOCARDIAL ISCHEMIA (insufficient blood supply to the heart muscle) caused by a decreased capacity of the coronary vessels.	2.38	2
Metabolic Acidosis [description not available]	1.98	1
Anoxemia [description not available]	1.98	1
Hyperpotassemia [description not available]	1.98	1
Acidosis A pathologic condition of acid accumulation or depletion of base in the body. The two main types are RESPIRATORY ACIDOSIS and metabolic acidosis, due to metabolic acid build up.	1.98	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	1.98	1
Hyperkalemia Abnormally high potassium concentration in the blood, most often due to defective renal excretion. It is characterized clinically by electrocardiographic abnormalities (elevated T waves and depressed P waves, and eventually by atrial asystole). In severe cases, weakness and flaccid paralysis may occur. (Dorland, 27th ed)	1.98	1
Anochlesia [description not available]	1.97	1
Muscle Contraction A process leading to shortening and/or development of tension in muscle tissue. Muscle contraction occurs by a sliding filament mechanism whereby actin filaments slide inward among the myosin filaments.	2.37	2
Ache [description not available]	1.97	1
Pain An unpleasant sensation induced by noxious stimuli which are detected by NERVE ENDINGS of NOCICEPTIVE NEURONS.	1.97	1

16-methylcyprenorphine

Description

Cross-References

Synonyms (9)

Research Excerpts

Dosage Studied

Research

Studies (12)

Market Indicators

Research Demand Index: 11.81

Study Types