Page last updated: 2024-11-13

AM2201

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

1-(5-fluoropentyl)-3-(1-naphthoyl)indole: a cannabimimetic; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	53393997
CHEMBL ID	3526578
CHEBI ID	185785
SCHEMBL ID	15703451

Synonyms (37)

Synonym
chembl3526578 ,
bdbm50088439
FT-0661542
CHEBI:185785
am2201
335161-24-5
[1-(5-luoropentyl)indol-3-yl]-naphthalen-1-ylmethanone
[1-(5-fluoropentyl)-1h-indol-3-yl]-1-naphthalenylmethanone
A20540
(1-(5-fluoropentyl)-1h-indol-3-yl)(naphthalen-1-yl)methanone;am-2201
(1-(5-fluoropentyl)-1h-indol-3-yl)(naphthalen-1-yl)methanone
AKOS015950753
unii-tbj0966f1o
jwh 2201
am 2201
(1-(5-fluoropentyl)-3-(1-naphthoyl)indole)
tbj0966f1o ,
dea no. 7201
am-2201
j2.973.653g ,
methanone, (1-(5-fluoropentyl)-1h-indol-3-yl)-1-naphthalenyl-
jwh-2201
CCG-208747
1-(5-fluoropentyl)-3-(1-naphthoyl)indole
[1-(5-fluoropentyl)indol-3-yl]-naphthalen-1-ylmethanone
SCHEMBL15703451
ALQFAGFPQCBPED-UHFFFAOYSA-N
gtpl9705
DTXSID50187158
am-2201 ((1-(5-fluoropentyl)indol-3-yl)(naphthalen-1-yl)methanone) 1.0 mg/ml in acetonitrile
am-2201; (1-(5-fluoropentyl)indol-3-yl)(naphthalen-1-yl)methanone; [1-(5-fluoropentyl)-1h-indol-3-yl]-1-naphthalenylmethanone
am-2201 ((1-(5-fluoropentyl)indol-3-yl)(naphthalen-1-yl)methanone)
am-2201 ((1-(5-fluoropentyl)indol-3-yl)(naphthalen-1-yl)methanone) 0.1 mg/ml in acetonitrile
Q4652489
methanone,[1-(5-fluoropentyl)-1h-indol-3-yl]-1-naphthalenyl-
am-2201, 0.1mg/ml in methanol
am-2201, 1mg/ml in methanol

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
indolecarboxamide
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (14)

Assay ID	Title	Year	Journal	Article
AID1211541	Drug metabolism in human urine assessed as (1-(5-fluoro-4-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone formation by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211519	Drug metabolism assessed as human recombinant CYP2E1-mediated (1-(5-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone formation at 10 uM after 90 mins by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211522	Drug metabolism assessed as human recombinant CYP3A4-mediated (1-(5-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone formation at 10 uM after 90 mins by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211526	Drug metabolism assessed as human recombinant CYP3A4-mediated (1-(5-fluoro-4-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone formation at 10 uM after 90 mins by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211525	Drug metabolism assessed as human recombinant CYP2E1-mediated (1-(5-fluoro-4-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone formation at 10 uM after 90 mins by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211520	Drug metabolism assessed as human recombinant CYP2E1-mediated 5-(3-(1-naphthoyl)-1H-indol-1-yl)pentanoic acid formation at 10 uM after 90 mins by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211515	Activation of CB1 receptor in B6SJL mouse brain membrane assessed as [35S]-GTPgammaS binding at 10 uM after 30 mins by liquid scintillation spectrophotometric analysis in presence of O-2050	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211523	Drug metabolism assessed as human recombinant CYP3A4-mediated 5-(3-(1-naphthoyl)-1H-indol-1-yl)pentanoic acid formation at 10 uM after 90 mins by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211513	Displacement of [3H]CP-55,940 from CB1 receptor in B6SJL mouse brain membrane after 90 mins by liquid scintillation spectrophotometric analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211514	Activation of CB1 receptor in B6SJL mouse brain membrane assessed as [35S]-GTPgammaS binding at 10 uM after 30 mins by liquid scintillation spectrophotometric analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211539	Drug metabolism in human urine assessed as 5-(3-(1-naphthoyl)-1H-indol-1-yl)pentanoic acid formation by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1211540	Drug metabolism in human urine assessed as (1-(5-hydroxypentyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone formation by LC-MS/MS analysis	2012	Drug metabolism and disposition: the biological fate of chemicals, Nov, Volume: 40, Issue:11	Cytochrome P450-mediated oxidative metabolism of abused synthetic cannabinoids found in K2/Spice: identification of novel cannabinoid receptor ligands.
AID1346701	Human CB1 receptor (Cannabinoid receptors)	2015	ACS chemical neuroscience, Aug-19, Volume: 6, Issue:8	Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135.
AID1346728	Human CB2 receptor (Cannabinoid receptors)	2015	ACS chemical neuroscience, Aug-19, Volume: 6, Issue:8	Effects of bioisosteric fluorine in synthetic cannabinoid designer drugs JWH-018, AM-2201, UR-144, XLR-11, PB-22, 5F-PB-22, APICA, and STS-135.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	27 (100.00)	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]

Market Indicators

Research Demand Index: 39.41

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	39.41 (24.57)
Research Supply Index	3.33 (2.92)
Research Growth Index	4.51 (4.65)
Search Engine Demand Index	56.46 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (39.41)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (3.70%)	6.00%
Case Studies	2 (7.41%)	4.05%
Observational	0 (0.00%)	0.25%
Other	24 (88.89%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
sulfaphenazole Sulfaphenazole: A sulfonilamide anti-infective agent.. sulfaphenazole : A sulfonamide that is sulfanilamide in which the sulfonamide nitrogen is substituted by a 1-phenyl-1H-pyrazol-5-yl group. It is a selective inhibitor of cytochrome P450 (CYP) 2C9 isozyme, and antibacterial agent.	7.08	1	primary amino compound; pyrazoles; substituted aniline; sulfonamide antibiotic; sulfonamide	antibacterial drug; EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor; EC 1.14.13.67 (quinine 3-monooxygenase) inhibitor; P450 inhibitor
n-pentanoic acid n-pentanoic acid: RN given refers to unlabeled parent cpd. valeric acid : A straight-chain saturated fatty acid containing five carbon atoms.	2.55	2	short-chain fatty acid; straight-chain saturated fatty acid	plant metabolite
indazoles Indazoles: A group of heterocyclic aromatic organic compounds consisting of the fusion of BENZENE and PYRAZOLES.	2.53	2	indazole
adamantane Adamantane: A tricyclo bridged hydrocarbon.	2.53	2	adamantanes; polycyclic alkane
methamphetamine Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.	2.08	1	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
alpha-naphthoflavone alpha-naphthoflavone: inhibits P4501A1 and P4501A2; stimulates some activities of P4503A4. alpha-naphthoflavone : An extended flavonoid resulting from the formal fusion of a benzene ring with the h side of flavone. A synthetic compound, it is an inhibitor of aromatase (EC 1.14.14.14).	2.08	1	extended flavonoid; naphtho-gamma-pyrone; organic heterotricyclic compound	aryl hydrocarbon receptor agonist; aryl hydrocarbon receptor antagonist; EC 1.14.14.14 (aromatase) inhibitor
dronabinol Dronabinol: A psychoactive compound extracted from the resin of Cannabis sativa (marihuana, hashish). The isomer delta-9-tetrahydrocannabinol (THC) is considered the most active form, producing characteristic mood and perceptual changes associated with this compound.. Delta(9)-tetrahydrocannabinol : A diterpenoid that is 6a,7,8,10a-tetrahydro-6H-benzo[c]chromene substituted at position 1 by a hydroxy group, positions 6, 6 and 9 by methyl groups and at position 3 by a pentyl group. The principal psychoactive constituent of the cannabis plant, it is used for treatment of anorexia associated with AIDS as well as nausea and vomiting associated with cancer chemotherapy.	3.02	4	benzochromene; diterpenoid; phytocannabinoid; polyketide	cannabinoid receptor agonist; epitope; hallucinogen; metabolite; non-narcotic analgesic
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.17	1	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
sr141716 [no description available]	2.15	1	amidopiperidine; carbohydrazide; dichlorobenzene; monochlorobenzenes; pyrazoles	anti-obesity agent; appetite depressant; CB1 receptor antagonist
cp-55,940 [no description available]	2.07	1
am 694 1-(5-fluoropentyl)-3-(2-iodobenzoyl)indole : A member of the class of indoles that is 1H-indole which is substituted at position 1 by a 5-fluoropentyl group and a position 3 by an o-fluorobenzoyl group. It is a selective agonist for the CB1 cannabinoid receptor; Ki values for the CB1 and CB2 receptors are 0.08 and 1.44 nM, respectively.	2.17	1	aromatic ketone; indoles; organofluorine compound; organoiodine compound; synthetic cannabinoid	cannabinoid receptor agonist
jwh 018 1-pentyl-3-(1-naphthoyl)indole: structure in first source	5.34	16	indolecarboxamide
jwh-073 [no description available]	9.14	4	indolecarboxamide
piperidines Piperidines: A family of hexahydropyridines.	2.15	1
jwh-122 (4-methyl-1-naphthyl)-(1-pentylindol-3-yl)methanone: structure in first source	3.03	4
ur-144 (1-pentyl-1H-indol-3-yl)(2,2,3,3-tetramethylcyclopropyl)methanone: structure in first source	3.03	4
jwh-210 4-ethylnaphthalen-1-yl-(1-pentylindol-3-yl)methanone: a cannabimimetic; structure in first source	7.78	3	indolecarboxamide
methylone [no description available]	2.08	1	benzodioxoles
n,n-diallyl-5-methoxytryptamine N,N-diallyl-5-methoxytryptamine: structure in first source	2.1	1	tryptamines
jwh 019 (1-hexyl-1H-indol-3-yl)-1-naphthalenylmethanone: a synthetic cannabinoid; structure in first source	2.54	2
sts-135 N-(adamantan-1-yl)-1-(5-fluoropentyl)-1H-indole-3-carboxamide: a synthetic cannabinoid; structure in first source	7.11	1	indolecarboxamide
xlr-11 XLR-11: synthetic cannabinoid; structure in first source	3.06	4
pentedrone pentedrone: structure in first source	2.08	1
am4113 AM4113: a cannabinoid CB1 receptor neutral antagonist	2.15	1
1-pentyl-1h-indole-3-carboxylic acid 8-quinolinyl ester 1-pentyl-1H-indole-3-carboxylic acid 8-quinolinyl ester: a recreational synthetic cannabinoid; structure in first source	2.11	1
n-(1-adamantyl)-1-(5-fluoropentyl)-1h-indazole-3-carboxamide N-(1-adamantyl)-1-(5-fluoropentyl)-1H-indazole-3-carboxamide: a cannabinoid receptor agonist; structure in first source	2.15	1	aromatic amide; indazoles
n-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1h-indazole-3-carboxamide N-(1-amino-3,3-dimethyl-1-oxobutan-2-yl)-1-pentyl-1H-indazole-3-carboxamide: a synthetic cannabinoid known as black mamba	2.11	1

Condition	Relationship Strength	Studies
Hypothermia, Accidental [description not available]	3.45	2
Hypothermia Lower than normal body temperature, especially in warm-blooded animals.	3.45	2
Anochlesia [description not available]	2.17	1
Absence Seizure [description not available]	3.48	2
Seizures Clinical or subclinical disturbances of cortical function due to a sudden, abnormal, excessive, and disorganized discharge of brain cells. Clinical manifestations include abnormal motor, sensory and psychic phenomena. Recurrent seizures are usually referred to as EPILEPSY or seizure disorder.	8.48	2
Wounds, Stab Penetrating wounds caused by a pointed object.	2.08	1
Injuries, Neck [description not available]	2.08	1
Chemical Dependence [description not available]	4.27	6
Substance-Related Disorders Disorders related to substance use or abuse.	4.27	6
Sensitivity and Specificity Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)	2.11	1
Dementia Praecox [description not available]	2.1	1
Schizophrenia A severe emotional disorder of psychotic depth characteristically marked by a retreat from reality with delusion formation, HALLUCINATIONS, emotional disharmony, and regressive behavior.	2.1	1
Adipocere [description not available]	2.11	1
Behavior Disorders [description not available]	3.06	1
Drug Withdrawal Symptoms [description not available]	3.06	1
Mental Disorders Psychiatric illness or diseases manifested by breakdowns in the adaptational process expressed primarily as abnormalities of thought, feeling, and behavior producing either distress or impairment of function.	3.06	1
Substance Withdrawal Syndrome Physiological and psychological symptoms associated with withdrawal from the use of a drug after prolonged administration or habituation. The concept includes withdrawal from smoking or drinking, as well as withdrawal from an administered drug.	3.06	1

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