Chemical Formula: C12H16N2O

Chemical Formula C12H16N2O

Found 87 metabolite its formula value is C12H16N2O

Bufotenin

3-(2-(Dimethylamino)ethyl)-1H-indol-5-ol (acd/name 4.0)

C12H16N2O (204.12625659999998)


A hallucinogenic serotonin analog found in frog or toad skins, mushrooms, higher plants, and mammals, especially in the brains, plasma, and urine of schizophrenics. Bufotenin has been used as a tool in CNS studies and misused as a psychedelic. Bufotenin (5-OH-DMT), is a tryptamine related to the neurotransmitter serotonin. It is an alkaloid found in the skin of some species of toads; in mushrooms, higher plants, and mammals. Bufotenin is a chemical constituent in the venom and eggs of several species of toads belonging to the Bufo genus, but most notably in the Colorado River toad (Bufo alvarius) as it is the only toad species in which bufotenin is present in large enough quantities for a psychoactive effect. Extracts of toad venom, containing bufotenin and other bioactive compounds, have been used in some traditional medicines (probably derived from Bufo gargarizans), which has been used medicinally for centuries in China. Bufotenin is a constituent of the seeds of Anadenanthera colubrina and Anadenanthera peregrina trees. Anadenanthera seeds have been used as an ingredient in psychedelic snuff preparations by indigenous cultures of the Caribbean, Central and South America. D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens D009676 - Noxae > D011042 - Poisons > D014688 - Venoms

   

Psilocin

3-[2-(Dimethylamino)ethyl]-1H-indol-4-ol

C12H16N2O (204.12625659999998)


Psilocin (4-OH-DMT), an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances. The mind-altering effects of psilocin are highly variable and subjective, but resemble those caused by LSD and mescaline. The effects typically last anywhere from three to eight hours depending on certain variables (such as metabolism, food interaction); however the effects can seem to last much longer due to psilocins ability to distort the perception of time. Sulfur analogs are known with a benzothienyl replacement as well as 4-SH-DMT. N1-methylpsilocin is a functionally 5-HT2C receptor preferring agonists. 4-fluoro-N,N-dimethyltryptamine is known. O-Acetylpsilocin is an acetylized analog of psilocin, also known as 4-AcO-DMT. Additionally, substitution of a methyl group at the dimethylated nitrogen with an isopropyl or ethyl group yields 4-HO-MIPT (4-Hydroxy-N-Methyl-N-Isopropyltryptamine) and 4-HO-MET (4-Hydroxy-N-Methyl-N-Ethyltryptamine), respectively. D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens

   

Caulophylline

(-)-N-methylcytisine

C12H16N2O (204.12625659999998)


N-Methylcytisine (Caulophylline), a tricyclic quinolizidine alkaloid, exerts hypoglycaemic, analgesic and anti-inflammatory activities. N-methylcytisine is a selective ligand of nicotinic receptors of acetylcholine in the central nervous system and has a high affinity (Kd = 50 nM) to nicotinic acetylcholine receptors (nAChR) from squid optical ganglia[1][2]. N-Methylcytisine (Caulophylline), a tricyclic quinolizidine alkaloid, exerts hypoglycaemic, analgesic and anti-inflammatory activities. N-methylcytisine is a selective ligand of nicotinic receptors of acetylcholine in the central nervous system and has a high affinity (Kd = 50 nM) to nicotinic acetylcholine receptors (nAChR) from squid optical ganglia[1][2]. N-Methylcytisine (Caulophylline), a tricyclic quinolizidine alkaloid, exerts hypoglycaemic, analgesic and anti-inflammatory activities. N-methylcytisine is a selective ligand of nicotinic receptors of acetylcholine in the central nervous system and has a high affinity (Kd = 50 nM) to nicotinic acetylcholine receptors (nAChR) from squid optical ganglia[1][2].

   

Nebracetam

4-(aminomethyl)-1-benzylpyrrolidin-2-one

C12H16N2O (204.12625659999998)


D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010277 - Parasympathomimetics D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs C26170 - Protective Agent > C1509 - Neuroprotective Agent

   

Caulophyllin

1,5-METHANO-8H-PYRIDO(1,2-A)(1,5)DIAZOCIN-8-ONE, 1,2,3,4,5,6-HEXAHYDRO-3-METHYL-, (1R,5S)-

C12H16N2O (204.12625659999998)


N-Methylcytisine is a natural product found in Thermopsis lanceolata, Sophora chrysophylla, and other organisms with data available. N-Methylcytisine (Caulophylline), a tricyclic quinolizidine alkaloid, exerts hypoglycaemic, analgesic and anti-inflammatory activities. N-methylcytisine is a selective ligand of nicotinic receptors of acetylcholine in the central nervous system and has a high affinity (Kd = 50 nM) to nicotinic acetylcholine receptors (nAChR) from squid optical ganglia[1][2]. N-Methylcytisine (Caulophylline), a tricyclic quinolizidine alkaloid, exerts hypoglycaemic, analgesic and anti-inflammatory activities. N-methylcytisine is a selective ligand of nicotinic receptors of acetylcholine in the central nervous system and has a high affinity (Kd = 50 nM) to nicotinic acetylcholine receptors (nAChR) from squid optical ganglia[1][2]. N-Methylcytisine (Caulophylline), a tricyclic quinolizidine alkaloid, exerts hypoglycaemic, analgesic and anti-inflammatory activities. N-methylcytisine is a selective ligand of nicotinic receptors of acetylcholine in the central nervous system and has a high affinity (Kd = 50 nM) to nicotinic acetylcholine receptors (nAChR) from squid optical ganglia[1][2].

   
   

UNII:U5XOB9AQ15

5-Methoxy-alpha-methyltryptamine

C12H16N2O (204.12625659999998)


   
   
   
   

(1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-dien-6-one

(1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.0<2,7>]trideca-2,4-dien-6-one

C12H16N2O (204.12625659999998)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.084 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.090

   

1-(4-phenylpiperazin-1-yl)ethanone

1-(4-phenylpiperazin-1-yl)ethanone

C12H16N2O (204.12625659999998)


   

1-(3,5-dimethylphenyl)piperazin-2-one

1-(3,5-dimethylphenyl)piperazin-2-one

C12H16N2O (204.12625659999998)


   

(3-AMINO-PHENYL)-PIPERIDIN-1-YL-METHANONE

(3-AMINO-PHENYL)-PIPERIDIN-1-YL-METHANONE

C12H16N2O (204.12625659999998)


   

4-CHLORO-5-IODO-6-METHYL-2-PYRIMIDINAMINE

4-CHLORO-5-IODO-6-METHYL-2-PYRIMIDINAMINE

C12H16N2O (204.12625659999998)


   
   
   

1-(2,3-DIHYDROBENZOFURAN-4-YL)PIPERAZINE

1-(2,3-DIHYDROBENZOFURAN-4-YL)PIPERAZINE

C12H16N2O (204.12625659999998)


   

(R)-1-AMINO-3-(9H-CARBAZOL-4-YLOXY)-2-PROPANOL

(R)-1-AMINO-3-(9H-CARBAZOL-4-YLOXY)-2-PROPANOL

C12H16N2O (204.12625659999998)


   

3-(n-(2-hydroxyethyl)-m-toluidino)propionitrile

3-(n-(2-hydroxyethyl)-m-toluidino)propionitrile

C12H16N2O (204.12625659999998)


   
   

6-(PIPERIDIN-1-YLMETHYL)PICOLINALDEHYDE

6-(PIPERIDIN-1-YLMETHYL)PICOLINALDEHYDE

C12H16N2O (204.12625659999998)


   

3-[3-(dimethylamino)propoxy]benzonitrile

3-[3-(dimethylamino)propoxy]benzonitrile

C12H16N2O (204.12625659999998)


   

1-(3-DIMETHYLAMINO-PROPYL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID

1-(3-DIMETHYLAMINO-PROPYL)-5-OXO-PYRROLIDINE-3-CARBOXYLIC ACID

C12H16N2O (204.12625659999998)


   

1-(4-piperazin-1-ylphenyl)ethanone

1-(4-piperazin-1-ylphenyl)ethanone

C12H16N2O (204.12625659999998)


   
   

6-amino-1,4,4-trimethyl-3H-quinolin-2-one

6-amino-1,4,4-trimethyl-3H-quinolin-2-one

C12H16N2O (204.12625659999998)


   

(4-AMINO-PHENYL)-MORPHOLIN-4-YL-METHANONE

(4-AMINO-PHENYL)-MORPHOLIN-4-YL-METHANONE

C12H16N2O (204.12625659999998)


   

PIPERIDINE-3-CARBOXYLIC ACID PHENYLAMIDE

PIPERIDINE-3-CARBOXYLIC ACID PHENYLAMIDE

C12H16N2O (204.12625659999998)


   

3-[2-(Dimethylamino)ethyl]-1H-indol-6-ol

3-[2-(Dimethylamino)ethyl]-1H-indol-6-ol

C12H16N2O (204.12625659999998)


   

1-BENZYL-PYRROLIDINE-3-CARBOXYLIC ACID AMIDE

1-BENZYL-PYRROLIDINE-3-CARBOXYLIC ACID AMIDE

C12H16N2O (204.12625659999998)


   
   

3-(4-Methylpiperazin-1-yl)benzaldehyde

3-(4-Methylpiperazin-1-yl)benzaldehyde

C12H16N2O (204.12625659999998)


   

N-(4-(Pyrrolidin-1-yl)phenyl)acetamide

N-(4-(Pyrrolidin-1-yl)phenyl)acetamide

C12H16N2O (204.12625659999998)


   
   

1-(8-amino-2,3,4,5-tetrahydro-1-benzazepin-1-yl)ethanone

1-(8-amino-2,3,4,5-tetrahydro-1-benzazepin-1-yl)ethanone

C12H16N2O (204.12625659999998)


   
   

2-(Piperidin-1-yl-carbonyl)-aniline

2-(Piperidin-1-yl-carbonyl)-aniline

C12H16N2O (204.12625659999998)


   

2-[3-(dimethylamino)propoxy]benzonitrile

2-[3-(dimethylamino)propoxy]benzonitrile

C12H16N2O (204.12625659999998)


   
   

4-[3-(dimethylamino)propoxy]benzonitrile

4-[3-(dimethylamino)propoxy]benzonitrile

C12H16N2O (204.12625659999998)


   
   

(R)-1-BENZYL-3-N-BOC-AMINOMETHYLPYRROLIDINE

(R)-1-BENZYL-3-N-BOC-AMINOMETHYLPYRROLIDINE

C12H16N2O (204.12625659999998)


   

(4-aminomethyl-phenyl)-pyrrolidin-1-yl-methanone

(4-aminomethyl-phenyl)-pyrrolidin-1-yl-methanone

C12H16N2O (204.12625659999998)


   

1-(pyridin-3-ylmethyl)piperidine-4-carbaldehyde

1-(pyridin-3-ylmethyl)piperidine-4-carbaldehyde

C12H16N2O (204.12625659999998)


   
   

1-(2-METHYL-2-PHENYLPROPYL)HYDRAZINE

1-(2-METHYL-2-PHENYLPROPYL)HYDRAZINE

C12H16N2O (204.12625659999998)


   
   

(3-METHYL-5-PHENYL-4-ISOXAZOLYL)METHANOL

(3-METHYL-5-PHENYL-4-ISOXAZOLYL)METHANOL

C12H16N2O (204.12625659999998)


   

2-Ethyl-1-(2-methoxyethyl)-1H-benzimidazole

2-Ethyl-1-(2-methoxyethyl)-1H-benzimidazole

C12H16N2O (204.12625659999998)


   

1H-Benzimidazole,5-ethoxy-1-ethyl-2-methyl-(9CI)

1H-Benzimidazole,5-ethoxy-1-ethyl-2-methyl-(9CI)

C12H16N2O (204.12625659999998)


   

2-(2-(1H-Indol-3-yl)ethylamino)ethanol

2-(2-(1H-Indol-3-yl)ethylamino)ethanol

C12H16N2O (204.12625659999998)


   
   

4-TERT-BUTOCYCARBONYLAMINO CYCLOHEXANE CARBOXYLIC ACID METHYL ESTER

4-TERT-BUTOCYCARBONYLAMINO CYCLOHEXANE CARBOXYLIC ACID METHYL ESTER

C12H16N2O (204.12625659999998)


   

N-(2-ethyl-6-methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine

N-(2-ethyl-6-methylphenyl)-4,5-dihydro-1,3-oxazol-2-amine

C12H16N2O (204.12625659999998)


   

(R)-2-HYDROXYMETHYLMORPHOLINE-4-CARBOXYLICACIDTERT-BUTYLESTER

(R)-2-HYDROXYMETHYLMORPHOLINE-4-CARBOXYLICACIDTERT-BUTYLESTER

C12H16N2O (204.12625659999998)


   

1-(4-methoxy-1h-indol-3-yl)-n,n-dimethylmethanamine

1-(4-methoxy-1h-indol-3-yl)-n,n-dimethylmethanamine

C12H16N2O (204.12625659999998)


   

1-(6-amino-3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)ethan-1-one

1-(6-amino-3,3-dimethyl-2,3-dihydro-1H-indol-1-yl)ethan-1-one

C12H16N2O (204.12625659999998)


   

2-(4-Methyl-1-piperazinyl)benzaldehyde

2-(4-Methyl-1-piperazinyl)benzaldehyde

C12H16N2O (204.12625659999998)


   

3-(1-ETHYL-1H-BENZIMIDAZOL-2-YL)PROPAN-1-OL

3-(1-ETHYL-1H-BENZIMIDAZOL-2-YL)PROPAN-1-OL

C12H16N2O (204.12625659999998)


   

3-(2,5-DIOXO-4-PHENYL-IMIDAZOLIDIN-4-YL)-PROPIONIC ACID

3-(2,5-DIOXO-4-PHENYL-IMIDAZOLIDIN-4-YL)-PROPIONIC ACID

C12H16N2O (204.12625659999998)


   

1H-Benzimidazole,5-ethoxy-2-propyl-(9CI)

1H-Benzimidazole,5-ethoxy-2-propyl-(9CI)

C12H16N2O (204.12625659999998)


   
   
   

1-(3-ACETYL-2-HYDROXY-5-METHYL-PHENYL)-ETHANONE

1-(3-ACETYL-2-HYDROXY-5-METHYL-PHENYL)-ETHANONE

C12H16N2O (204.12625659999998)


   
   
   

4-(4-Methylpiperazin-1-yl)benzaldehyde

4-(4-Methylpiperazin-1-yl)benzaldehyde

C12H16N2O (204.12625659999998)


   

2-(5,6-dimethyl-1H-benzoimidazol-2-yl)propan-2-ol

2-(5,6-dimethyl-1H-benzoimidazol-2-yl)propan-2-ol

C12H16N2O (204.12625659999998)


   

4,7,8-Trimethyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one

4,7,8-Trimethyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-2-one

C12H16N2O (204.12625659999998)


   

1-[(4-Methylphenyl)methyl]-1,3-diazinan-2-one

1-[(4-Methylphenyl)methyl]-1,3-diazinan-2-one

C12H16N2O (204.12625659999998)


   

2-(5-Methoxy-2-methyl-1H-indol-3-yl)ethanamine

2-(5-Methoxy-2-methyl-1H-indol-3-yl)ethanamine

C12H16N2O (204.12625659999998)


   

N-(3-methylphenyl)cyclobutanecarbohydrazide

N-(3-methylphenyl)cyclobutanecarbohydrazide

C12H16N2O (204.12625659999998)


   

(1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

(1S,9S)-11-methyl-7,11-diazatricyclo[7.3.1.02,7]trideca-2,4-dien-6-one

C12H16N2O (204.12625659999998)


   

[(1R,2aS,8bS)-2-methyl-2a,3,4,8b-tetrahydro-1H-azeto[2,3-c]quinolin-1-yl]methanol

[(1R,2aS,8bS)-2-methyl-2a,3,4,8b-tetrahydro-1H-azeto[2,3-c]quinolin-1-yl]methanol

C12H16N2O (204.12625659999998)


   

[(1R,2aR,8bR)-2-methyl-2a,3,4,8b-tetrahydro-1H-azeto[2,3-c]quinolin-1-yl]methanol

[(1R,2aR,8bR)-2-methyl-2a,3,4,8b-tetrahydro-1H-azeto[2,3-c]quinolin-1-yl]methanol

C12H16N2O (204.12625659999998)


   

[(1S,2aS,8bS)-2-methyl-2a,3,4,8b-tetrahydro-1H-azeto[2,3-c]quinolin-1-yl]methanol

[(1S,2aS,8bS)-2-methyl-2a,3,4,8b-tetrahydro-1H-azeto[2,3-c]quinolin-1-yl]methanol

C12H16N2O (204.12625659999998)


   

PSILOCIN

PSILOCIN

C12H16N2O (204.12625659999998)


A tryptamine alkaloid that is N,N-dimethyltryptamine carrying an additional hydroxy substituent at position 4. A hallucinogenic alkaloid isolated in trace amounts from Psilocybe mushrooms (also known as Teonanacatl or "magic mushrooms"). D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens

   

bufotenin

Bufotenine

C12H16N2O (204.12625659999998)


A tertiary amine that consists of N,N-dimethyltryptamine bearing an additional hydroxy substituent at position 5. D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D012702 - Serotonin Antagonists D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D006213 - Hallucinogens D009676 - Noxae > D011042 - Poisons > D014688 - Venoms

   

(1r,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

(1r,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

C12H16N2O (204.12625659999998)


   

(1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

(1s,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

C12H16N2O (204.12625659999998)


   

(1r,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

(1r,9s)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

C12H16N2O (204.12625659999998)


   
   

[(7-methoxy-1h-indol-3-yl)methyl]dimethylamine

[(7-methoxy-1h-indol-3-yl)methyl]dimethylamine

C12H16N2O (204.12625659999998)


   

(1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

(1s,9r)-11-methyl-7,11-diazatricyclo[7.3.1.0²,⁷]trideca-2,4-dien-6-one

C12H16N2O (204.12625659999998)