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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 13:48:30 UTC
Update Date2022-11-23 22:29:16 UTC
HMDB IDHMDB0254474
Secondary Accession NumbersNone
Metabolite Identification
Common NameMescaline
Descriptionmescaline, also known as TMPEA, belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine. mescaline is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a small amount of articles have been published on mescaline. This compound has been identified in human blood as reported by (PMID: 31557052 ). Mescaline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Mescaline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
Thumb
Synonyms
ValueSource
1-Amino-2-(3,4,5-trimethoxyphenyl)ethaneChEBI
3,4,5-TrimethoxybenzeneethanamineChEBI
3,4,5-TrimethoxyphenethylamineChEBI
3,4,5-TrimethoxyphenylethylamineChEBI
MescalinChEBI
MescalinaChEBI
MeskalinChEBI
MezcalinaChEBI
TMPEAChEBI
MezcalinMeSH
PeyoteMeSH
TrimethoxyphenethylamineMeSH
Chemical FormulaC11H17NO3
Average Molecular Weight211.261
Monoisotopic Molecular Weight211.120843411
IUPAC Name2-(3,4,5-trimethoxyphenyl)ethan-1-amine
Traditional Namemescaline
CAS Registry NumberNot Available
SMILES
COC1=CC(CCN)=CC(OC)=C1OC
InChI Identifier
InChI=1S/C11H17NO3/c1-13-9-6-8(4-5-12)7-10(14-2)11(9)15-3/h6-7H,4-5,12H2,1-3H3
InChI KeyRHCSKNNOAZULRK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenethylamines. Phenethylamines are compounds containing a phenethylamine moiety, which consists of a phenyl group substituted at the second position by an ethan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentPhenethylamines
Alternative Parents
Substituents
  • Phenethylamine
  • Phenoxy compound
  • Anisole
  • 2-arylethylamine
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Aralkylamine
  • Ether
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Amine
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.91ALOGPS
logP0.91ChemAxon
logS-2.2ALOGPS
pKa (Strongest Basic)9.77ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area53.71 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity58.68 m³·mol⁻¹ChemAxon
Polarizability23.1 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+142.45930932474
DeepCCS[M-H]-139.62130932474
DeepCCS[M-2H]-176.12430932474
DeepCCS[M+Na]+151.66230932474
AllCCS[M+H]+148.332859911
AllCCS[M+H-H2O]+144.332859911
AllCCS[M+NH4]+152.032859911
AllCCS[M+Na]+153.132859911
AllCCS[M-H]-150.232859911
AllCCS[M+Na-2H]-151.032859911
AllCCS[M+HCOO]-152.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
mescalineCOC1=CC(CCN)=CC(OC)=C1OC2550.8Standard polar33892256
mescalineCOC1=CC(CCN)=CC(OC)=C1OC1815.6Standard non polar33892256
mescalineCOC1=CC(CCN)=CC(OC)=C1OC1707.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
mescaline,1TMS,isomer #1COC1=CC(CCN[Si](C)(C)C)=CC(OC)=C1OC1840.6Semi standard non polar33892256
mescaline,1TMS,isomer #1COC1=CC(CCN[Si](C)(C)C)=CC(OC)=C1OC1948.9Standard non polar33892256
mescaline,1TMS,isomer #1COC1=CC(CCN[Si](C)(C)C)=CC(OC)=C1OC2514.7Standard polar33892256
mescaline,2TMS,isomer #1COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2079.6Semi standard non polar33892256
mescaline,2TMS,isomer #1COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2120.9Standard non polar33892256
mescaline,2TMS,isomer #1COC1=CC(CCN([Si](C)(C)C)[Si](C)(C)C)=CC(OC)=C1OC2419.8Standard polar33892256
mescaline,1TBDMS,isomer #1COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2084.6Semi standard non polar33892256
mescaline,1TBDMS,isomer #1COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2134.6Standard non polar33892256
mescaline,1TBDMS,isomer #1COC1=CC(CCN[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2572.6Standard polar33892256
mescaline,2TBDMS,isomer #1COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2513.6Semi standard non polar33892256
mescaline,2TBDMS,isomer #1COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2497.9Standard non polar33892256
mescaline,2TBDMS,isomer #1COC1=CC(CCN([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=CC(OC)=C1OC2556.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Mescaline GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-6910000000-63b875b68510f431304a2021-09-24Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mescaline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 10V, Positive-QTOFsplash10-03dj-0890000000-616863bde223b3ac872c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 20V, Positive-QTOFsplash10-0002-0920000000-47fd07c5573212e7fc362019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 40V, Positive-QTOFsplash10-014i-5900000000-15a76f5868097c4890ed2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 10V, Negative-QTOFsplash10-03di-0090000000-fd2ca69e6cdbbf1a0a0c2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 20V, Negative-QTOFsplash10-03di-0890000000-83e2781633dd51c42f352019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 40V, Negative-QTOFsplash10-000i-2900000000-67896f160b9a42f4f3332019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 10V, Positive-QTOFsplash10-0002-0910000000-9a24a439b17db5331dfb2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 20V, Positive-QTOFsplash10-0002-0900000000-501fa4dae613a29636872021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 40V, Positive-QTOFsplash10-0ktb-3900000000-7dc0298d7f673f65aa0f2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 10V, Negative-QTOFsplash10-03di-0090000000-f0203d0d15365b0c06532021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 20V, Negative-QTOFsplash10-03di-0590000000-c63f9b5dcd00541ee2ce2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mescaline 40V, Negative-QTOFsplash10-0aor-9400000000-76523f7fb050748dbc112021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDC00001419
Chemspider ID3934
KEGG Compound IDC06546
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMescaline
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID28346
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. This receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. This receptor is involved in tracheal smooth muscle contraction, bronchoconstriction, and control of aldosterone production
Gene Name:
HTR2A
Uniprot ID:
P28223
Molecular weight:
52602.6
General function:
Not Available
Specific function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity).
Gene Name:
HTR2A
Uniprot ID:
Q5R4Q6
Molecular weight:
52528.45
General function:
Not Available
Specific function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity).
Gene Name:
HTR2A
Uniprot ID:
P50128
Molecular weight:
52602.58
General function:
Not Available
Specific function:
G-protein coupled receptor for 5-hydroxytryptamine (serotonin). Also functions as a receptor for various drugs and psychoactive substances, including mescaline, psilocybin, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane (DOI) and lysergic acid diethylamide (LSD). Ligand binding causes a conformation change that triggers signaling via guanine nucleotide-binding proteins (G proteins) and modulates the activity of down-stream effectors. Beta-arrestin family members inhibit signaling via G proteins and mediate activation of alternative signaling pathways. Signaling activates phospholipase C and a phosphatidylinositol-calcium second messenger system that modulates the activity of phosphatidylinositol 3-kinase and promotes the release of Ca(2+) ions from intracellular stores. Affects neural activity, perception, cognition and mood. Plays a role in the regulation of behavior, including responses to anxiogenic situations and psychoactive substances. Plays a role in intestinal smooth muscle contraction, and may play a role in arterial vasoconstriction (By similarity).
Gene Name:
HTR2A
Uniprot ID:
P50129
Molecular weight:
52675.595