Chemical Formula: C12H14N2O

Chemical Formula C12H14N2O

Found 115 metabolite its formula value is C12H14N2O

Tetrahydroharmol

2,3,4,9-Tetrahydro-1-methyl-1H-pyrido[3,4-b]indol-7-ol, 8ci

C12H14N2O (202.1106074)


Tetrahydroharmol is found in fruits. Tetrahydroharmol is an alkaloid from Elaeagnus angustifolia (Russian olive) Harmaline is a reversible inhibitor of MAO-A (RIMA). Harmine is a reversible inhibitor of MAO-A (RIMA). It is important to note that unlike synthetic pharmaceutical MAOIs such as phenelzine, harmine is reversible and selective meaning it does not have nearly as high a risk for the "cheese syndrome" caused by consuming tyramine-containing foods, which is a risk associated with monoamine oxidase A inhibitors, but not monoamine oxidase B inhibitors. Several alkaloids that function as monoamine oxidase inhibitors (MAOIs) are found in the seeds of Peganum harmala (also known as Harmal or Syrian Rue), including harmine, harmaline, and harmalol, which are members of a group of substances with a similar chemical structure collectively known as harmala alkaloids. These alkaloids are of interest for their use in Amazonian shamanism, where they are derived from other plants. The harmala alkaloid harmine which was once known as Telepathine and Banisterine is a naturally occurring beta-carboline alkaloid that is structurally related to harmaline, and also found in the vine Banisteriopsis caapi. Tetrahydroharmine is also found in B. caapi, but not P. harmala. Dr. Alexander Shulgin has suggesed that harmaline may be a breakdown product of harmine. Harmine and harmaline are reversible MAOIs of the MAO-A isoform of the enzyme, and can stimulate the central nervous system by inhibiting the metabolism of monoamine compounds such as serotonin and norepinephrine. The harmala alkaloids occur in Peganum harmala in concentrations of roughly 3\\%, though tests have documented anywhere from 2-7\\%, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the Banisteriopsis caapi vine, the key plant ingredient in the sacramental beverage Ayahuasca, in concentrations that range between 0.31-8.43\\% for harmine, 0.03-0.83\\% for harmaline and 0.05-2.94\\% for tetrahydroharmine. Other psychoactive plants are often added to Ayahuasca to achieve visionary states of consciousness; for example leaves from Psychotria viridis, which is a source of dimethyltryptamine (DMT). The harmala alkaloids serve to potentiate these brewed compounds by preventing their breakdown in the digestive tract. The harmala alkaloids are not especially psychoactive on their own, even at high dosages, when vomiting and diarrhea become the main effect

   

N-Methyl-1H-indole-3-propanamide

3-(1H-indol-3-yl)-N-Methylpropanimidate

C12H14N2O (202.1106074)


N-Methyl-1H-indole-3-propanamide is found in mushrooms. N-Methyl-1H-indole-3-propanamide is produced by Omphalotus olearius (common chanterelle). Production by Omphalotus olearius (common chanterelle). N-Methyl-1H-indole-3-propanamide is found in mushrooms.

   

6-Methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

C12H14N2O (202.1106074)


   

5-Methoxytryptoline

5-methoxy-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

C12H14N2O (202.1106074)


   

6-Hydroxytetrahydroharman

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-6-ol

C12H14N2O (202.1106074)


   

Gramineal

3-[(dimethylamino)methyl]-1H-indole-1-carbaldehyde

C12H14N2O (202.1106074)


   

N-Acetyltryptamine

N-Acetyltryptamine monohydrochloride

C12H14N2O (202.1106074)


   

THbetaC

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-5-ol

C12H14N2O (202.1106074)


D009676 - Noxae > D009498 - Neurotoxins

   

7Z,14Z-eicosadienoic acid

(1S)-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-6-ol

C12H14N2O (202.1106074)


   

1-Methylspiro[indoline-3,3-pyrrolidin]-2-one

1-Methylspiro[indoline-3,3-pyrrolidin]-2-one

C12H14N2O (202.1106074)


   
   

6-Hydroxy-1-methyl-1,2,3,4-tetrahydro-beta-carboline

6-Hydroxy-1-methyl-1,2,3,4-tetrahydro-beta-carboline

C12H14N2O (202.1106074)


   

Benzenemethanol, 3-(1H-imidazol-4-ylmethyl)-2-methyl-

Benzenemethanol, 3-(1H-imidazol-4-ylmethyl)-2-methyl-

C12H14N2O (202.1106074)


   

N-Acetyltryptamine

NCGC00015088-09_C12H14N2O_N-[2-(1H-Indol-3-yl)ethyl]acetamide

C12H14N2O (202.1106074)


   
   

3H-Indol-3-one, 2-(1-aminobutyl)-

3H-Indol-3-one, 2-(1-aminobutyl)-

C12H14N2O (202.1106074)


   

6-METHOXY-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE

6-methoxy-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

C12H14N2O (202.1106074)


D002491 - Central Nervous System Agents > D000927 - Anticonvulsants

   
   
   

Peganine hydrochloride

Peganine hydrochloride

C12H14N2O (202.1106074)


   

4-Hydrocynewbouldine|4-hydroxynewbouldine

4-Hydrocynewbouldine|4-hydroxynewbouldine

C12H14N2O (202.1106074)


   

N-(2-(1H-Indol-3-yl)ethyl)-N-methylformamide

N-(2-(1H-Indol-3-yl)ethyl)-N-methylformamide

C12H14N2O (202.1106074)


   

6-Hydroxytetrahydroharman

6-Hydroxytetrahydroharman

C12H14N2O (202.1106074)


   

Tetrahydroharmol

2,3,4,9-Tetrahydro-1-methyl-1H-pyrido[3,4-b]indol-7-ol, 8ci

C12H14N2O (202.1106074)


   

N-Methyl-1H-indole-3-propanamide

3-(1H-indol-3-yl)-N-methylpropanamide

C12H14N2O (202.1106074)


   

C-[3-(3,5-DIMETHYL-PHENYL)-ISOXAZOL-5-YL]-METHYLAMINE

C-[3-(3,5-DIMETHYL-PHENYL)-ISOXAZOL-5-YL]-METHYLAMINE

C12H14N2O (202.1106074)


   

4-(Morpholinomethyl)benzonitrile

4-(Morpholinomethyl)benzonitrile

C12H14N2O (202.1106074)


   

2-(3-Piperidinyloxy)benzonitrile

2-(3-Piperidinyloxy)benzonitrile

C12H14N2O (202.1106074)


   

3-piperidin-4-yloxybenzonitrile

3-piperidin-4-yloxybenzonitrile

C12H14N2O (202.1106074)


   

3-Methyl-1-(3,4-dimethylphenyl)-2-pyrazolin-5-one

3-Methyl-1-(3,4-dimethylphenyl)-2-pyrazolin-5-one

C12H14N2O (202.1106074)


   

1,5-Dimethyl-2-(p-tolyl)-1H-pyrazol-3(2H)-one

1,5-Dimethyl-2-(p-tolyl)-1H-pyrazol-3(2H)-one

C12H14N2O (202.1106074)


   

2-(PIPERIDIN-3-YL)BENZO[D]OXAZOLE HYDROCHLORIDE

2-(PIPERIDIN-3-YL)BENZO[D]OXAZOLE HYDROCHLORIDE

C12H14N2O (202.1106074)


   

2-(3,4-DIMETHYL-PHENYL)-OXAZOL-4-YL-METHYLAMINE

2-(3,4-DIMETHYL-PHENYL)-OXAZOL-4-YL-METHYLAMINE

C12H14N2O (202.1106074)


   

5-(TETRAHYDRO-PYRAN-4-YL)-1H-INDAZOLE

5-(TETRAHYDRO-PYRAN-4-YL)-1H-INDAZOLE

C12H14N2O (202.1106074)


   

2(1H)-Quinolinone,7-(dimethylamino)-4-methyl-

2(1H)-Quinolinone,7-(dimethylamino)-4-methyl-

C12H14N2O (202.1106074)


   

Spiro[indoline-3,4-piperidin]-2-one

Spiro[indoline-3,4-piperidin]-2-one

C12H14N2O (202.1106074)


   

Acetamide,2-cyano-N-(2,4,6-trimethylphenyl)-

Acetamide,2-cyano-N-(2,4,6-trimethylphenyl)-

C12H14N2O (202.1106074)


   

3-(dimethylamino)-2-(4-methoxyphenyl)acrylonitrile

3-(dimethylamino)-2-(4-methoxyphenyl)acrylonitrile

C12H14N2O (202.1106074)


   

1-(1-ETHYL-2-METHYL-1H-BENZO[D]IMIDAZOL-5-YL)ETHANONE

1-(1-ETHYL-2-METHYL-1H-BENZO[D]IMIDAZOL-5-YL)ETHANONE

C12H14N2O (202.1106074)


   

4-Benzyl-2-morpholinecarbonitrile

4-Benzyl-2-morpholinecarbonitrile

C12H14N2O (202.1106074)


   

2-(2,5-DIMETHYL-1H-PYRROL-1-YL)-5-METHOXYPYRIDINE

2-(2,5-DIMETHYL-1H-PYRROL-1-YL)-5-METHOXYPYRIDINE

C12H14N2O (202.1106074)


   

3-Piperidin-4-yl-benzo[d]isoxazole

3-Piperidin-4-yl-benzo[d]isoxazole

C12H14N2O (202.1106074)


   

4-(1H-indol-6-yl)morpholine

4-(1H-indol-6-yl)morpholine

C12H14N2O (202.1106074)


   

2-(2-m-tolylpropan-2-yl)-1,3,4-oxadiazole

2-(2-m-tolylpropan-2-yl)-1,3,4-oxadiazole

C12H14N2O (202.1106074)


   

5-ethyl-1-methyl-2-phenylpyrazol-3-one

5-ethyl-1-methyl-2-phenylpyrazol-3-one

C12H14N2O (202.1106074)


   

N-METHYL-N-[(5-METHYL-3-PHENYLISOXAZOL-4-YL)METHYL]AMINE

N-METHYL-N-[(5-METHYL-3-PHENYLISOXAZOL-4-YL)METHYL]AMINE

C12H14N2O (202.1106074)


   

3-(3-Phenyl-1H-pyrazol-5-yl)-1-propanol

3-(3-Phenyl-1H-pyrazol-5-yl)-1-propanol

C12H14N2O (202.1106074)


   
   

3-butylquinazolin-4-one

3-butylquinazolin-4-one

C12H14N2O (202.1106074)


   

2-piperidin-4-yl-benzooxazole

2-piperidin-4-yl-benzooxazole

C12H14N2O (202.1106074)


   

4-[(3,5-DIMETHYL-1H-PYRAZOL-4-YL)METHYL]BENZENOL

4-[(3,5-DIMETHYL-1H-PYRAZOL-4-YL)METHYL]BENZENOL

C12H14N2O (202.1106074)


   

5-Isopropyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

5-Isopropyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

C12H14N2O (202.1106074)


   

2-(morpholin-4-ylmethyl)benzonitrile

2-(morpholin-4-ylmethyl)benzonitrile

C12H14N2O (202.1106074)


   

4-Morpholineacetonitrile,a-phenyl-

4-Morpholineacetonitrile,a-phenyl-

C12H14N2O (202.1106074)


   

2-(2-ETHYL-PHENYL)-OXAZOL-4-YL-METHYLAMINE

2-(2-ETHYL-PHENYL)-OXAZOL-4-YL-METHYLAMINE

C12H14N2O (202.1106074)


   

N-[(3-methyl-1,2-oxazol-5-yl)methyl]-1-phenylmethanamine

N-[(3-methyl-1,2-oxazol-5-yl)methyl]-1-phenylmethanamine

C12H14N2O (202.1106074)


   

(4-METHOXY-BENZYL)-PYRIDIN-3-YLMETHYL-AMINE

(4-METHOXY-BENZYL)-PYRIDIN-3-YLMETHYL-AMINE

C12H14N2O (202.1106074)


   

4-Cyano-2-isopropylacetanilide

4-Cyano-2-isopropylacetanilide

C12H14N2O (202.1106074)


   

2-(1H-indol-3-yl)morpholine

2-(1H-indol-3-yl)morpholine

C12H14N2O (202.1106074)


   

4-(4-HYDROXY-PIPERIDIN-1-YL)-BENZONITRILE

4-(4-HYDROXY-PIPERIDIN-1-YL)-BENZONITRILE

C12H14N2O (202.1106074)


   

2-(3,4-Dimethylphenyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one

2-(3,4-Dimethylphenyl)-1,2-dihydro-5-methyl-3H-pyrazol-3-one

C12H14N2O (202.1106074)


   

2,3,4,5-TETRAHYDRO-8-METHOXY-1H-PYRIDO[4,3-B]INDOLE

2,3,4,5-TETRAHYDRO-8-METHOXY-1H-PYRIDO[4,3-B]INDOLE

C12H14N2O (202.1106074)


   

N-METHYL-(4-METHYL-2-PHENYL-1,3-OXAZOL-5-YLMETHYL)AMINE

N-METHYL-(4-METHYL-2-PHENYL-1,3-OXAZOL-5-YLMETHYL)AMINE

C12H14N2O (202.1106074)


   

6-amino-6,7,8,9-tetrahydro-5H-carbazol-3-ol

6-amino-6,7,8,9-tetrahydro-5H-carbazol-3-ol

C12H14N2O (202.1106074)


   

1-(6-Aminospiro[cyclopropane-1,3-indolin]-1-yl)ethanone

1-(6-Aminospiro[cyclopropane-1,3-indolin]-1-yl)ethanone

C12H14N2O (202.1106074)


   

1-ETHYL-5-METHYL-4-PHENYLIMIDAZOLIN-2-ONE

1-ETHYL-5-METHYL-4-PHENYLIMIDAZOLIN-2-ONE

C12H14N2O (202.1106074)


   

1-(2-isocyanatophenyl)piperidine

1-(2-isocyanatophenyl)piperidine

C12H14N2O (202.1106074)


   

4-[3-(DIMETHYLAMINO)PROP-1-YNYL]BENZALDEHYDE OXIME

4-[3-(DIMETHYLAMINO)PROP-1-YNYL]BENZALDEHYDE OXIME

C12H14N2O (202.1106074)


   

N,N-Diallylnicotinamide

N,N-Diallylnicotinamide

C12H14N2O (202.1106074)


   
   

2-BROMO-3-CHLOROTOLUENE

2-BROMO-3-CHLOROTOLUENE

C12H14N2O (202.1106074)


   

(2-METHOXY-BENZYL)-THIOUREA

(2-METHOXY-BENZYL)-THIOUREA

C12H14N2O (202.1106074)


   

8-Methoxy-2,4-dimethyl-1H-1,5-benzodiazepine

8-Methoxy-2,4-dimethyl-1H-1,5-benzodiazepine

C12H14N2O (202.1106074)


   

2-(4-HYDROXY-PIPERIDIN-1-YL)-BENZONITRILE

2-(4-HYDROXY-PIPERIDIN-1-YL)-BENZONITRILE

C12H14N2O (202.1106074)


   

5-methyl-2-(2-phenylethyl)-4H-pyrazol-3-one

5-methyl-2-(2-phenylethyl)-4H-pyrazol-3-one

C12H14N2O (202.1106074)


   

1-(2-METHYLAMINOETHYL)ADAMANTANEHYDROCHLORIDE

1-(2-METHYLAMINOETHYL)ADAMANTANEHYDROCHLORIDE

C12H14N2O (202.1106074)


   

1,3-diethylquinoxalin-2-one

1,3-diethylquinoxalin-2-one

C12H14N2O (202.1106074)


   

1-(4-isocyanatophenyl)piperidine

1-(4-isocyanatophenyl)piperidine

C12H14N2O (202.1106074)


   

1H-Pyrido[4,3-b]indol-4-ol, 2,3,4,5-tetrahydro-2-methyl-

1H-Pyrido[4,3-b]indol-4-ol, 2,3,4,5-tetrahydro-2-methyl-

C12H14N2O (202.1106074)


   

3-(p-Formyl-N-ethylanilino)propionitrile

3-(p-Formyl-N-ethylanilino)propionitrile

C12H14N2O (202.1106074)


   

3-[3-(DIMETHYLAMINO)PROP-1-YNYL]BENZALDEHYDE OXIME

3-[3-(DIMETHYLAMINO)PROP-1-YNYL]BENZALDEHYDE OXIME

C12H14N2O (202.1106074)


   

4-(4-Piperidinyloxy)benzonitrile

4-(4-Piperidinyloxy)benzonitrile

C12H14N2O (202.1106074)


   

N-METHYL-N-[(5-METHYL-2-PHENYL-1,3-OXAZOL-4-YL)METHYL]AMINE

N-METHYL-N-[(5-METHYL-2-PHENYL-1,3-OXAZOL-4-YL)METHYL]AMINE

C12H14N2O (202.1106074)


   

3-(morpholin-4-ylmethyl)benzonitrile

3-(morpholin-4-ylmethyl)benzonitrile

C12H14N2O (202.1106074)


   

3-(3-Piperidinyloxy)benzonitrile

3-(3-Piperidinyloxy)benzonitrile

C12H14N2O (202.1106074)


   

1,2,3,6,7,11SS-HEXAHYDRO-4H-PYRAZINO[2,1-A]ISOQUINOLINE-4-ONE

1,2,3,6,7,11SS-HEXAHYDRO-4H-PYRAZINO[2,1-A]ISOQUINOLINE-4-ONE

C12H14N2O (202.1106074)


   

1-(3,4-dimethylphenyl)-3-methyl-1H-pyrazol-5-ol

1-(3,4-dimethylphenyl)-3-methyl-1H-pyrazol-5-ol

C12H14N2O (202.1106074)


   

2-((S)-3-Hydroxy-pyrrolidin-1-ylMethyl)-benzonitrile

2-((S)-3-Hydroxy-pyrrolidin-1-ylMethyl)-benzonitrile

C12H14N2O (202.1106074)


   
   

5-PROPYL-3-(P-TOLYL)-1,2,4-OXADIAZOLE

5-PROPYL-3-(P-TOLYL)-1,2,4-OXADIAZOLE

C12H14N2O (202.1106074)


   

2-(cyclohexyloxy)nicotinonitrile

2-(cyclohexyloxy)nicotinonitrile

C12H14N2O (202.1106074)


   

1-BENZYL-4,5-DIMETHYLIMIDAZOLE-3-OXIDE

1-BENZYL-4,5-DIMETHYLIMIDAZOLE-3-OXIDE

C12H14N2O (202.1106074)


   

1-[(4-Ethylbenzyl)oxy]-1H-imidazole

1-[(4-Ethylbenzyl)oxy]-1H-imidazole

C12H14N2O (202.1106074)


   

1-(1-Isopropyl-1H-pyrrolo[2,3-c]pyridin-3-yl)ethanone

1-(1-Isopropyl-1H-pyrrolo[2,3-c]pyridin-3-yl)ethanone

C12H14N2O (202.1106074)


   

6-(TETRAHYDRO-PYRAN-4-YL)-1H-INDAZOLE

6-(TETRAHYDRO-PYRAN-4-YL)-1H-INDAZOLE

C12H14N2O (202.1106074)


   

4-(3-Piperidinyloxy)benzonitrile

4-(3-Piperidinyloxy)benzonitrile

C12H14N2O (202.1106074)


   

2-(4-Piperidinyloxy)benzonitrile

2-(4-Piperidinyloxy)benzonitrile

C12H14N2O (202.1106074)


   

8-Methoxy-N-methyl-5-quinolinemethanamine

8-Methoxy-N-methyl-5-quinolinemethanamine

C12H14N2O (202.1106074)


   

4-(4-CYANOPHENYL)-4-HYDROXYPIPERIDINE

4-(4-CYANOPHENYL)-4-HYDROXYPIPERIDINE

C12H14N2O (202.1106074)


   

4-(2-HYDROXYETHYL)AMINO-2-METHYLQUINOLINE

4-(2-HYDROXYETHYL)AMINO-2-METHYLQUINOLINE

C12H14N2O (202.1106074)


   

N,N-dimethyl(5-(pyridin-3-yl)furan-2-yl)methanamine

N,N-dimethyl(5-(pyridin-3-yl)furan-2-yl)methanamine

C12H14N2O (202.1106074)


   

3-(1H-indol-3-yl)-N-methylpropanamide

3-(1H-indol-3-yl)-N-methylpropanamide

C12H14N2O (202.1106074)


   

4-[(3s,3as)-3h,3ah,4h,5h,6h-pyrrolo[1,2-b]pyrazol-3-yl]phenol

4-[(3s,3as)-3h,3ah,4h,5h,6h-pyrrolo[1,2-b]pyrazol-3-yl]phenol

C12H14N2O (202.1106074)


   

3-(1h-indol-3-yl)-n-methylpropanimidic acid

3-(1h-indol-3-yl)-n-methylpropanimidic acid

C12H14N2O (202.1106074)


   

(1s)-1-methyl-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-7-ol

(1s)-1-methyl-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-7-ol

C12H14N2O (202.1106074)


   

7-methoxy-1h,2h,3h,4h,9h-pyrido[3,4-b]indole

7-methoxy-1h,2h,3h,4h,9h-pyrido[3,4-b]indole

C12H14N2O (202.1106074)


   

(1r)-1-methyl-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-6-ol

(1r)-1-methyl-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-6-ol

C12H14N2O (202.1106074)


   

4-{3h,3ah,4h,5h,6h-pyrrolo[1,2-b]pyrazol-3-yl}phenol

4-{3h,3ah,4h,5h,6h-pyrrolo[1,2-b]pyrazol-3-yl}phenol

C12H14N2O (202.1106074)


   

(3s)-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol

(3s)-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol

C12H14N2O (202.1106074)


   

1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol

1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol

C12H14N2O (202.1106074)


   

n-[2-(1h-indol-3-yl)ethyl]ethanimidic acid

n-[2-(1h-indol-3-yl)ethyl]ethanimidic acid

C12H14N2O (202.1106074)


   

n-[2-(1h-indol-3-yl)ethyl]-n-methylformamide

n-[2-(1h-indol-3-yl)ethyl]-n-methylformamide

C12H14N2O (202.1106074)


   

(3r)-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol

(3r)-1'-methylspiro[indole-3,3'-pyrrolidin]-2-ol

C12H14N2O (202.1106074)


   

3-methyl-6h,7h,8h,9h-pyridazino[1,2-a]indazol-1-one

3-methyl-6h,7h,8h,9h-pyridazino[1,2-a]indazol-1-one

C12H14N2O (202.1106074)


   

4-[(3r,3ar)-3h,3ah,4h,5h,6h-pyrrolo[1,2-b]pyrazol-3-yl]phenol

4-[(3r,3ar)-3h,3ah,4h,5h,6h-pyrrolo[1,2-b]pyrazol-3-yl]phenol

C12H14N2O (202.1106074)