Penniclavine

{{Chembox

| ImageFile = Penniclavine.svg

| ImageSize = 150px

| ImageAlt =

| IUPACName = 8β-(Hydroxymethyl)-6-methyl-9,10-didehydroergolin-8α-ol

| SystematicName = (6aR,9S)-9-(Hydroxymethyl)-7-methyl-4,6,6a,7,8,9-hexahydroindolo[4,3-fg]quinolin-9-ol

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 519-13-1

| CASNo_Ref = {{cascite|correct|CAS}}

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 28Z5OY3SFA

| PubChem = 115247

| ChemSpiderID = 103117

| SMILES = OC[C@]3(O)/C=C2/c4cccc1c4c(c[nH]1)C[C@H]2N(C3)C

| InChI = 1/C16H18N2O2/c1-18-8-16(20,9-19)6-12-11-3-2-4-13-15(11)10(7-17-13)5-14(12)18/h2-4,6-7,14,17,19-20H,5,8-9H2,1H3/t14-,16+/m1/s1

| InChIKey = KCHBNRCSCHMJFD-ZBFHGGJFBY

| StdInChI = 1S/C16H18N2O2/c1-18-8-16(20,9-19)6-12-11-3-2-4-13-15(11)10(7-17-13)5-14(12)18/h2-4,6-7,14,17,19-20H,5,8-9H2,1H3/t14-,16+/m1/s1

| StdInChIKey = KCHBNRCSCHMJFD-ZBFHGGJFSA-N

}}

|Section2={{Chembox Properties

| C=16 | H=18 | N=2 | O=2

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|Section3={{Chembox Hazards

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Penniclavine is an ergot alkaloid that has been found in morning glory species such as Argyreia nervosa (Hawaiian baby woodrose).{{cite journal | vauthors = Bacon CW, Porter JK, Robbins JD | title = Laboratory production of ergot alkaloids by species of balansia | journal = J Gen Microbiol | volume = 113 | issue = 1 | pages = 119–126 | date = July 1979 | pmid = 501329 | doi = 10.1099/00221287-113-1-119 | doi-access = free | url = }}{{cite journal | vauthors = Paulke A, Kremer C, Wunder C, Wurglics M, Schubert-Zsilavecz M, Toennes SW | title = Studies on the alkaloid composition of the Hawaiian Baby Woodrose Argyreia nervosa, a common legal high | journal = Forensic Sci Int | volume = 249 | issue = | pages = 281–293 | date = April 2015 | pmid = 25747328 | doi = 10.1016/j.forsciint.2015.02.011 | url = }}{{cite journal | vauthors = Hylin JW, Watson DP | title = Ergoline Alkaloids in Tropical Wood Roses | journal = Science | volume = 148 | issue = 3669 | pages = 499–500 | date = April 1965 | pmid = 17842841 | doi = 10.1126/science.148.3669.499 | bibcode = 1965Sci...148..499H | url = }} It was first described by the 1950s.