Butorphanol (CED0003032)

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:15 UTC

Update Date

2026-08-21 19:51:56 UTC

SynCED ID

CED0003032

Secondary Accession Numbers

CHEM002229
T3D2837

Identification

Common Name

Butorphanol

Class

Small Molecule

Description

Butorphanol is an exogenous compound with the formula C21H29NO2 and an average molecular weight of 327.46 g/mol. It exists as a solid at room temperature. Butorphanol belongs to the phenanthrenes and derivatives, a class of benzenoids within the organic compounds. This compound is used as an opioid analgesic and an antitussive. It functions as a kappa-opioid receptor agonist and a mu-opioid receptor agonist. Its recorded protein targets include the kappa-type opioid receptor (OPRK1), the mu-type opioid receptor (OPRM1), and the delta-type opioid receptor (OPRD1). Butorphanol is a mixed agonist-antagonist with low intrinsic activity at receptors of the mu-opioid type (morphine-like) and acts as an agonist at kappa-opioid receptors. Most of its pharmacologic effects, including analgesia, are apparently mediated by its interactions with these receptors in the central nervous system. Butorphanol is found in sources including pharmaceuticals and veterinary products used as analgesics, as well as electrical and electronic equipment such as antennas. Recorded routes of exposure for the compound include intravenous, intramuscular, and nasal administration.

Contaminant Type

Amine
Analgesic, Opioid
Antitussive Agent
Drug
Human Neurotoxin
Metabolite
Narcotic
Narcotic Antagonist
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Not Available

Chemical Formula

C₂₁H₂₉NO₂

Average Molecular Mass

327.461 g/mol

Monoisotopic Mass

327.220 g/mol

CAS Registry Number

42408-82-2

IUPAC Name

Not Available

Traditional Name

Not Available

SMILES

[H][C@@]12CC3=C(C=C(O)C=C3)[C@]3(CCCC[C@@]13O)CCN2CC1CCC1

InChI Identifier

InChI=1S/C21H29NO2/c23-17-7-6-16-12-19-21(24)9-2-1-8-20(21,18(16)13-17)10-11-22(19)14-15-4-3-5-15/h6-7,13,15,19,23-24H,1-5,8-12,14H2/t19-,20+,21-/m1/s1

InChI Key

IFKLAQQSCNILHL-QHAWAJNXSA-N

Chemical Taxonomy

Classification

Not classified

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	272-274°C
Boiling Point	Not Available
Solubility	Moderate

Predicted Properties

Not Available

Spectra

Not Available

Toxicity Profile

Toxicity Values

Toxicity Value	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Toxicity Rating	Reference
659.0 Log mg/kg [370:1200]	Rat	LD50	oral	predicted	Not Available	Not Available

Toxicity / Toxin Class

Not Available

Mechanism of Toxicity

The exact mechanism of action is unknown, but is believed to interact with an opiate receptor site in the CNS (probably in or associated with the limbic system). The opiate antagonistic effect may result from competitive inhibition at the opiate receptor, but may also be a result of other mechanisms. Butorphanol is a mixed agonist-antagonist that exerts antagonistic or partially antagonistic effects at mu opiate receptor sites, but is thought to exert its agonistic effects principally at the kappa and sigma opiate receptors. Its interactions with these receptors in the central nervous system apparently mediate most of its pharmacologic effects, including analgesia.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Minimum Risk Level

Not Available

Symptoms

The clinical manifestations of butorphanol overdose are those of opioid drugs in general. The most serious symptoms are hypoventilation, cardiovascular insufficiency, coma, and death. Medical problems can include congested lungs, liver disease, tetanus, infection of the heart valves, skin abscesses, anemia and pneumonia. Death can occur from overdose.

Treatment

The management of suspected butorphanol overdosage includes maintenance of adequate ventilation, peripheral perfusion, normal body temperature, and protection of the airway. Patients should be under continuous observation with adequate serial measures of mental state, responsiveness, and vital signs. Oxygen and ventilatory assistance should be available with continual monitoring by pulse oximetry if indicated. In the presence of coma, placement of an artificial airway may be required. An adequate intravenous portal should be maintained to facilitate treatment of hypotension associated with vasodilation. The use of a specific opioid antagonist such as naloxone should be considered. As the duration of butorphanol action usually exceeds the duration of action of naloxone, repeated dosing with naloxone may be required. (3)

Health Effects

Health Effect	Relationship	Direction	Description	Reference

Exposure Sources

Source ID	Source	Sector	Reference
CEDs000010	Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.	Agriculture & land management	PubChem
CEDs000370	Analgesics?Analgesics are a class of synthetic chemicals designed to alleviate pain.	Healthcare, pharmaceuticals & veterinary products	Not Available
CEDs000506	Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.	Electrical & Electronic Equipment	PubChem
CEDs000511	Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.	Electrical & Electronic Equipment	PubChem
CEDs000517	Electric Switches?Electric switches, integral components in numerous devices, can be a source of synthetic chemical contamination due to the materials and manufacturing processes involved in their production.	Electrical & Electronic Equipment	PubChem
CEDs000518	Electrically Stimulated Smoking Devices?Electrically stimulated smoking devices, commonly known as e-cigarettes or vape pens, utilize electrical components to heat a liquid solution, often containing nicotine, flavorings, and other additives, to produce an aerosol for inhalation.	Electrical & Electronic Equipment	PubChem
CEDs000545	Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.	Food, food processing & cookware	PubChem
CEDs000556	Cigar Cigarettes?Cigar cigarettes are a source of synthetic chemical contamination due to the combustion of various tobacco blends and additives.	Household cleaning & consumer products	PubChem
CEDs000569	Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.	Household cleaning & consumer products	PubChem
CEDs000580	Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.	Industrial manufacturing & chemical processing	PubChem
CEDs000581	Paper Making Machines?Paper making machines utilize various synthetic chemicals throughout the production process, including additives, coatings, and bleaching agents.	Industrial manufacturing & chemical processing	PubChem
CEDs000596	Acaricides?Acaricides are synthetic chemicals specifically designed to target and control mite populations that can damage crops and plants.	Agriculture & land management	PubChem
CEDs000605	Pest Repellants?Pest repellents, often formulated from synthetic chemicals, are widely used to protect crops from insect infestations and other pests.	Agriculture & land management	PubChem
CEDs000610	Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.	Personal care & cosmetics	PubChem
CEDs000611	Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.	Personal care & cosmetics	PubChem
CEDs000632	Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.	Textiles, leather & furnishings	PubChem
CEDs000650	Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.	Textiles, leather & furnishings	PubChem
CEDs000671	Airplanes And Helicopters?Airplanes and helicopters are significant sources of synthetic chemical contamination primarily through the use of aviation fuels, lubricants, and de-icing agents.	Aviation & Aerospace	PubChem
CEDs000685	Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.	Building & Construction	PubChem
CEDs000696	Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.	Industrial manufacturing & chemical processing	PubChem
CEDs000698	Jewellery?Jewellery production often involves the use of various synthetic chemicals during the extraction and processing of metals.	Mining & metal processing	PubChem
CEDs000735	Explosives?Explosives are chemical compounds or mixtures designed to undergo rapid decomposition, releasing energy in the form of gas and heat.	Defense & military infrastructure	PubChem
CEDs000740	Paper?Paper production involves the processing of wood fibers and the use of various chemicals, which can lead to synthetic chemical contamination.	Paper, pulp & fiber products	PubChem
CEDs000744	Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.	Wastewater, sanitation & biosolids	PubChem

Pathways

2 pathwaysPathway Source: PathBank

Butorphanol Opioid Antagonist Action Pathway

Butorphanol Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Kappa-type opioid receptor	P41144	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.497 Applicability Domain 0.578 Statistical Significance 0.0079 Supporting Reference Compounds 199 E-value 61.3452
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Predicted (SEA)	Prediction Confidence Score 0.481 Applicability Domain 0.552 Statistical Significance 0.0111 Supporting Reference Compounds 532 E-value 86.6462
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Predicted (SEA)	Prediction Confidence Score 0.481 Applicability Domain 0.552 Statistical Significance 0.0122 Supporting Reference Compounds 427 E-value 94.9761
Click to view 3D structure	Mu-type opioid receptor	P97266	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.455 Applicability Domain 0.508 Statistical Significance 0.0127 Supporting Reference Compounds 186 E-value 99.1799
Click to view 3D structure	Delta-type opioid receptor	P32300	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.449 Applicability Domain 0.578 Statistical Significance 0.0125 Supporting Reference Compounds 166 E-value 97.3894
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Predicted (SEA)	Prediction Confidence Score 0.447 Applicability Domain 0.508 Statistical Significance 0.0151 Supporting Reference Compounds 527 E-value 117.708
Click to view 3D structure	Mu-type opioid receptor	P42866	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.437 Applicability Domain 0.578 Statistical Significance 0.0058 Supporting Reference Compounds 107 E-value 44.8412
Click to view 3D structure	Kappa-type opioid receptor	P33534	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.394 Applicability Domain 0.416 Statistical Significance 0.0077 Supporting Reference Compounds 61 E-value 60.0996
Click to view 3D structure	Delta-type opioid receptor	P33533	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.389 Applicability Domain 0.4 Statistical Significance 0.0177 Supporting Reference Compounds 164 E-value 137.482
Click to view 3D structure	Mu-type opioid receptor	P33535	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.386 Applicability Domain 0.4 Statistical Significance 0.0229 Supporting Reference Compounds 229 E-value 177.963
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q60492	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.365 Applicability Domain 0.375 Statistical Significance 0.0119 Supporting Reference Compounds 229 E-value 93.0298
Click to view 3D structure	Kappa-type opioid receptor	P34975	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.363 Applicability Domain 0.4 Statistical Significance 0.0157 Supporting Reference Compounds 66 E-value 122.223
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q99720	Humans	Predicted (SEA)	Prediction Confidence Score 0.361 Applicability Domain 0.375 Statistical Significance 0.022 Supporting Reference Compounds 562 E-value 171.346
Click to view 3D structure	D(2) dopamine receptor	P61169	Rat	Predicted (SEA)	Prediction Confidence Score 0.361 Applicability Domain 0.375 Statistical Significance 0.0216 Supporting Reference Compounds 528 E-value 168.544
Click to view 3D structure	Muscarinic acetylcholine receptor M2	P10980	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.36 Applicability Domain 0.375 Statistical Significance 0.0018 Supporting Reference Compounds 98 E-value 14.1686
Click to view 3D structure	Sigma intracellular receptor 2	Q5BJF2	Humans	Predicted (SEA)	Prediction Confidence Score 0.358 Applicability Domain 0.375 Statistical Significance 0.0097 Supporting Reference Compounds 308 E-value 75.2802
Click to view 3D structure	G_PROTEIN_RECEP_F1_2 domain-containing protein	F7HEV7	Macaca mulatta	Predicted (SEA)	Prediction Confidence Score 0.35 Applicability Domain 0.354 Statistical Significance 5.50e-04 Supporting Reference Compounds 3 E-value 4.28171
Click to view 3D structure	Kappa-type opioid receptor	H9FL65	Macaca mulatta	Predicted (SEA)	Prediction Confidence Score 0.35 Applicability Domain 0.354 Statistical Significance 5.50e-04 Supporting Reference Compounds 3 E-value 4.28171
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	Q9R0C9	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.34 Applicability Domain 0.348 Statistical Significance 0.0095 Supporting Reference Compounds 207 E-value 73.8789
Click to view 3D structure	Nociceptin receptor	P41146	Humans	Predicted (SEA)	Prediction Confidence Score 0.336 Applicability Domain 0.4 Statistical Significance 0.0157 Supporting Reference Compounds 73 E-value 122.613
Click to view 3D structure	G_PROTEIN_RECEP_F1_2 domain-containing protein	A0A286XTF2	Cavia porcellus	Predicted (SEA)	Prediction Confidence Score 0.33 Applicability Domain 0.475 Statistical Significance 4.80e-04 Supporting Reference Compounds 5 E-value 3.73676
Click to view 3D structure	Mu-type opioid receptor	P79350	Bos taurus	Predicted (SEA)	Prediction Confidence Score 0.328 Applicability Domain 0.413 Statistical Significance 0.0018 Supporting Reference Compounds 17 E-value 14.0907
Click to view 3D structure	Orexin/Hypocretin receptor type 1	O43613	Humans	Predicted (SEA)	Prediction Confidence Score 0.301 Applicability Domain 0.326 Statistical Significance 0.0059 Supporting Reference Compounds 70 E-value 46.1646
Click to view 3D structure	Sigma non-opioid intracellular receptor 1	O55242	Mus musculus	Predicted (SEA)	Prediction Confidence Score 0.301 Applicability Domain 0.371 Statistical Significance 9.30e-04 Supporting Reference Compounds 16 E-value 7.23998
Click to view 3D structure	Sigma intracellular receptor 2	Q5U3Y7	Rattus norvegicus	Predicted (SEA)	Prediction Confidence Score 0.3 Applicability Domain 0.348 Statistical Significance 0.0203 Supporting Reference Compounds 110 E-value 157.878
Click to view 3D structure	Sulfotransferase 2A1	Q06520	Humans	Known	Not Available
Click to view 3D structure	Mu-type opioid receptor	P35372	Humans	Known	Butorphanol is a mixed agonist-antagonist with low intrinsic activity at receptors of the µ-opioid type (morphine-like). It is also an agonist at κ-opioid receptors. Its interactions with these receptors in the central nervous system apparently mediate most of its pharmacologic effects, including analgesia.
Click to view 3D structure	Delta-type opioid receptor	P41143	Humans	Known	Butorphanol is a mixed agonist-antagonist with low intrinsic activity at receptors of the µ-opioid type (morphine-like). It is also an agonist at κ-opioid receptors. Its interactions with these receptors in the central nervous system apparently mediate most of its pharmacologic effects, including analgesia.
Click to view 3D structure	Kappa-type opioid receptor	P41145	Humans	Known	Butorphanol is a mixed agonist-antagonist with low intrinsic activity at receptors of the µ-opioid type (morphine-like). It is also an agonist at κ-opioid receptors. Its interactions with these receptors in the central nervous system apparently mediate most of its pharmacologic effects, including analgesia.

Concentrations

Not Available

External Links

Identifiers

Not Available

References

Synthesis Reference

Monkovic, I. and Conway, T.T.; U.S. Patent 3,775,414; November 27,1973; Monkovic, I.,Wong, H. and Lim, G.; U.S. Patent 3,980,641; September 14, 1976; Pachter, IJ., Belleau, B.R. and Monkovic, I.; U.S. Patent 3,819,635; June 25,1974; and Lim, G. and Hooper, J.W.; U.S. Patent 4,017,497; April 12,1977; all assigned to Bristol-Myers Company.

MSDS

Link

General References

Gear RW, Miaskowski C, Gordon NC, Paul SM, Heller PH, Levine JD: The kappa opioid nalbuphine produces gender- and dose-dependent analgesia and antianalgesia in patients with postoperative pain. Pain. 1999 Nov;83(2):339-45. [PubMed: 10534607]
Fan LW, Tanaka S, Tien LT, Ma T, Rockhold RW, Ho IK: Withdrawal from dependence upon butorphanol uniquely increases kappa(1)-opioid receptor binding in the rat brain. Brain Res Bull. 2002 Jun;58(2):149-60. [PubMed: 12127012]
RxList: The Internet Drug Index (2009). - http://www.rxlist.com/

Butorphanol (CED0003032)

Structure for CHEM002229: Butorphanol

Structure