21/9/2015
ErowidPsilocybinMushroomVault:Chemistry
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PsilocybinMushroomChemistry
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NAME:
CHEMICALNAME:
ALTERNATECHEMICALNAMES:
CHEMICALFORMULA
MOLECULARWEIGHT
MELTINGPOINT
MELTINGPOINT
Psilocybin
3[2(Dimethylamino)ethyl]1Hindol4oldihydrogenphosphateester
Ophosphoryl4hydroxyN,NdimethyltryptamineIndocybin
C12H17N2O4P
284.25
220228C(Crystalsfromboilingwater)
185195C(Crystalsfrommethanol)
pH
LD50
LD50
5.2(in50%aqethanol)
285mg/kgi.v.(mice)
280mg/kgi.v.(rats)
LD50
12.5mg/kgi.v.(rabbits)
FromtheMerckIndex12thEdition
NAME:
Psilocin
CHEMICALNAME:
3[2(Dimethylamino)ethyl]1Hindol4ol
ALTERNATECHEMICALNAMES: 4hydroxyN,Ndimethyltryptaminepsilocyn
CHEMICALFORMULA
C12H16N2O
MOLECULARWEIGHT
204.27
MELTINGPOINT
173176C(platesfrommethanol)
FromtheMerckIndex12thEdition
NAME:
Baeocystin
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21/9/2015
ErowidPsilocybinMushroomVault:Chemistry
CHEMICALNAME:
3[2(methylamino)ethyl]1Hindol4oldihydrogenphosphateester
ALTERNATECHEMICALNAMES: desmethylpsilocybine4phosphoryloxyNmethyltryptaminebaeocystin
CHEMICALFORMULA
C11H15N2O4P
MOLECULARWEIGHT
270.28
MELTINGPOINT
254258C(crystalsfrommethanol)
FromPharmacotheon
BriefBaeocystinInfo
PsilocybinExtractionNotes
MERCKINDEXENTRIES
[Link].3[2(Dimethylamino)ethyl]1Hindol4olOphosphoryl4hydroxyN,NdimethyltryptamineIndocybin.C 12H 17N 2O2Pmolwt284.25.C
50.71%,H6.03%,N9.86%,O22.51%,P10.90%.ThemajoroftwohallucinogeniccompoundsinTeonanacatl,thesacredmushroomofMexico,theother
componentbeingpsilocin,[Link],Agaricaceae:Hofmannetal.,Experientia14,107(1958)Heimetal.,
[Link].Acto42,1557(1959)Heimetal.,Gerpat.1,087,321(1960toSandoz).Structure:Hofmannetal.,Experientia14,397(1958).Synthesis:
Hofmann,Troxler,[Link].3,075,992(1963toSandoz).Crystalstructure:[Link],[Link],[Link].,PerkinTrans.II1974,[Link]
[Link]:[Link],[Link],PsychotropicDrugsandRelatedCompounds(NationalInstituteofMentalHealth,Rockville,Md.,2nd
ed.,1972)[Link]:Hofmann,[Link].,Rome1958,446Cerletti,[Link].84,2317(1959)Hofmann,
Bull.Narcotics23,3(1971).
CrystalsfromBoilingwater,mp220228fromboilingmethanol,[Link](methanol):220,267,290nm(logE4.6,3.8,3.6).pH5.2in50%aq
ethanol.Solin20partsboilingwater,[Link],benzene.LD50inmice,rats,rabbits
(mg/kg):285,280,12.5i.v.(Usdin,Efron).
Note:Thisisacontrolledsubstance(hallucinogen)[Link],Title21Part1308.11(1995).
THERAPCAT:Psychomimetic
[Link].3[2(Diumethylamino)ethyl]1Hindol4ol4hydroxyN,Ndimethyltryptaminepsilocyn.C 12H 16N 2Omolwt204.27.C70.56%,H7.89%,N
13.71%O7.83%.TheminorhallucinogeniccomponentofTeonanacatl,[Link]
PsilocybemexicanaHeim,Agaricaceae:Hofmannetal.,Experientia14,107(1948)Heimetal.,[Link].Acta42,1557(1959).Prepn:Heimetal.,Ger.
pat1,087,321(1960toSandoz).Syntheticprecursorofpsilocybin:Hofmann,Troxler,[Link].3,075,992(1963toSandoz).Psilocin,the4hydroxyanalog
ofpsilocybin,isformedbymetabolicdephosphoylationofpsilocybinandistheactivespeciesinthhcentralnervoussystem:Hoita,Weber,ToxicolAppl.
Pharmacol.4,730(1962).Crystalstructure:[Link],[Link],730(1962).Crystalstructure:[Link],[Link],[Link].
II1974,[Link],Bull.Narcotics23,3(1971)
Platesfrommethanol,[Link],[Link],260,267,283,
293nm(logE4.6,3.7,3.8,3.7,3.6).
Note:Thisisacontrolledsubstance(hallucinogen)[Link],Title21Part1308.11(1995).
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