Drug Enforcement Administration Microgram Bulletin , 1967-1970

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F'ro:rn the I:la.1reau orl

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, Drug Abuse ()ontrol/ •

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----------------------------------·--------·--------··----· ·:.1 S:>:\/!c:: s·Tii:.(TS ----··-T:1is is the first issue of our t'licro-Gram. ',!hen, anr, H,. tb::: n2xt issue

0e first heard about STP early in the Spring, 1j67 from articles in

underground newspapers. We also had reports that psychedelic promoters, such as Timot!~y Leary had refe·rred to a new ·hallucinogen cal Jed 11 ST?' 1, re~ortedly

stronger than LSO.

Late in 1\pril, tab1ets purported to contain the ne\'1 hallucinogen were acquired by 8QAC on the East and West coasts. In early June, al lege~ly s·':!vcr.J1 thot.tsand 11 STP 11 tablets ~vere distributed free at n ''LO\/E I:!' 1

in the San Francisco area. After this, we received reports, particularly on the 'Jest coast of many hospitalizations of people having bad trf~s from "STP.'' T:lr:! normal treatment forLSD, the tranquilizer Thorazine, seened to h:~ C•)J1~ r.~- i nd 'i c nt•:ld in treinols; E, caffein~roup; is classified under a pounds", include

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Buf"' . H This and similar hydroxytryptamines 4 have been synthesized by Stoll et al. (16). The article includes • Abstr. entry). ultraviolet and infrared spectra and a spot test (see Chern. -~--

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tir (Arnell) •Respazem (Zemmer) •Respazem No. 2 (Zemmer) Restinal Tablets (Sanford) •Restophen (Kay) . •Restophen Half-Strength (Noyes) Revamodex 15 and 60 (Rand) •Revicaps (Lederle) Revidex (Rand) Rhinalator(Amphetamine Sulfate) Rhinodex Tablets (Stanford) Ro-Dex (Rowell) •Rogesic (Rocky Mountain) •Rohist-Pius (Rocky Mountain) 01>Rotase (Northrup) fi!Rotase-Mitte (Northrup) •Rotran (Rocky Mountsin)

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Roxyn (Rocky Mountain) R-S-Tabs (Kare) •Rubarsin (Rupp and Bowman) Ruck-Sed (Rucker) '~>Ru-Ludin (Rudy Klein) utanol _ jRx No. 4087 (Zemmer) Terpy;Hnous (Lustgarten) Tetrahydrophenobarbital Tetrona! Theratone (Day-Baldwin) "'lheratone-B (Day-Baldwin) ®Thiabarb (Calc'weli and Bloor) henmetrazine (4) STP ···-r·· ...··

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N, N-dieth)11 tryptamine

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From the Archive Library of Erowid Center http://erowid.org/library/periodicals/microgram

\U Vol.I,No.8

Edited by Investigative Services Branch

May,l968

Psilocybin Analysis - Reference Doctor Wilcox, Chief, Bureau of Laboratories, and Dr. Howenstine, Division of Crime Detection, Michigan Department of Health, subi'~For reagents (1) & (2) see Bamford, Frank, Poisons 1 Their Isolation and Identification, 3rd edit., p. 248. For reagent (3) see A.O.A.C. lOth edit., 32.279(e), except that we have found that the reagent need not be prepared fresh daily as directed.

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/2{,.

THE IDENTIFICATION AND QUANTITATIVE DETERMINATION OF PSILOCYBIN IN TABLETS

d?y

Emil G. Siegmund and Robert J. Martin, Los Angeles District, FDA

Psilocybin [indol-4-ol,3-(2-(dimethylamine) ethyl)], a hallusinogenic drug occurring naturally in the mushroom P-scilocyba mexicana (1), has recently appeared on the illicit drug market. Pharmacologically, psilocybin and other LSD-type drugs both stimulate and depress the central nervous system, impairing coordination, judgment, and sense of time; the degree of reaction and duration of effects depend on the dosage used. Psilocybin is about 1/100 as potent as LSD and one tablet dose usually contains about 4-8 mg (2). Because of FDA's responsibilities under the Drug Abuse Control Act, a method is needed for identifying psilocybin and determining it quantitatively in unknown samples. Such a method has been developed and is given in detail below. In this procedure, psilocybin is extracted into methanol and the ultraviolet (UV) absorbance of the solution is determined at 268 rv; it is then compared with the characteristic UV spectrum of a standard psilocybin solution which has an absorptivity of 220 at 2'68 Illl· Psilocybin is further identified by thin layer chromatography (TLC). Method Reagents and Apparatus (a) Celite 545.-Acid-washed (3). (b)

Methanol~Anhydrous,

reagent grade.

(c) Mobile solvent.-Mix 50 ml 5% ammonium hydroxide. ·

~-propanol

(reagent grade) and 35 ml

(d) Chromogenic spray (Ehrlich's reagent).-5% solution of dimethylamine-benzaldehyde (Eastman 95) in concentrated HCl. (e) Psilocybin reference standard.-0.5 mg psilocybin (Sandoz Pharmaceutical, Hanover, N.J.) per 100.0 ml methanol (b). (f) Column.-Partition chromatography glass column ca 25 mm in diameter x 200 mm long.

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- 2 -

(g) TLC plates.-Put a 250 ll layer of silica gel G on plates 8 x 8". Dry for 30 min. at 80°C. Store in desiccator. Procedure Assay.-To a 100 ml beaker add powdered sample equivalent to 0.5 mg psilocybin,! g Celite, and 1 ml methanol, and mix thoroughly. Transfer· mixture to partition column containing a layer of a mixture of3 g Ce1ite and 2 ml methanol. Dry wash the beaker and transfer to column. Wipe beaker with pledget of glass wool and place on top of column. Pack entire column firmly, place a 100 ml volumetric flask under it, and elute with 95 ml methanol. Prepare a blank column (minus sample) as above and carry through the same procedure. Dilute to volume with methanol. Determine the UV spectrum from 330 to 230 miJ. in a 5 em silica cell vs. a methanol reference. Compare the spectrum with the standard solution spectrum at 2·68 ffi1J. by the base line technique and correct for blank. Calculate the amount of psilocybin in the sample. If the eluate is cloudy, the column has not been packed tightly enough. To remove this 'cloudiness, centrifuge at 2300 rpm for 10 min. Identification by TLC (1). -Spot from 2 to 4 IJ.g psilocybin (sample and standard) on a thin layer plate. Aliquots of sample and standard solution can be concentrated by air evaporation only. Develop the plate for 2 hr with the mobile solvent, remove plate from developing tank, and allow to dry. View under UV light. The psilocybin spots are faintly visible. Spray plate with chromogenic reagent. Psilocybin yields blueviolet spots with an Rf value of about 0.38. Discussion and Results In the above method, psilocybin was identified first by, its characteristic absorbance of UV light and second by TLC. p-Dimethylamino~ . benzaldehyde (T.S.) was tried as the chromogenic reagent for psilocybin but the resulting spots were a very pale yellow and difficult to see. Ehrlich's reagent was therefore used. (LSD had an ~f of 1.0 when chromatographed as above.) The following table summarizes the psylocybin recovery data for simulated tablet mixes, column recoveries and commercially prepared tablets.

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- 3 -

Table 1.

Psilocybin (PSC) recovery data Sample Compos it ion

Analyst

Recovered

Simulated Mixes

A

0.5 mg PSC/300 mg starch

101%, 102%

B

0.5 mg PSC/300 mg starch: talc (5: 1)

96%, 98%

Column Recoveries 0.42

A

mg

PSC added

99%, 103%

C?mmercial ~ablets (single tablet assay)~ A

0.5 mg PSC declared

0.5 mg

c

0.5 mg PSC declared

0.45 mg

~ TLC identification was positive for psilocybin.

\ Acknowledgment I

The authors wish to thank Donald Dechert for his assistance and collaboration. I

References

(1) Leung, A. Y., and Smith, A. H., J. Pharm. Sci., 54, 1576-1579 (1965). (2) Medicinal. Chemistry, A Series of Monographs: De Stevens, G. (Ed.) , Diuretics: Chemistry and Pharmacology, Vol. I, 1963; Maxwell, G. (Ed.), Psychopharmacological Agents. Vol. IV, 1964, PP• 556-574, Academic Press, New York and London. (3) United States Pharmacopeia, 17th Rev., Mack Publishing Co., Easton,

•

Pa., 1965, p. 192 •

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Vol.I, No.9

Edited by Investigative Services Branch

N-Methyl-3-Pieeridyl benzilate

h~drochloride

.June, 19.68

("JB-336 11 ~

We have examined four samples alleged to be "LBJ" and one sample alleged to be "TWA". Analysis shows them to be identical to N-Methyl-3-piperidyl benzilate hydrochloride, also known as "JB-336". The evidence analyzed has consisted of both capsules and powder. The capsules varied in size from No. 1 to No. 5. The compound has been off-lAThite with some containing specks of a blue, chloroform soluble dye.

OH I

C6H5

c

-

C6H5

..c

0

0

-o I

CH3

.HCl

The literature indicates that JB-336 is a potent an~i-cholinergic compound. Street doses will probably cause confusion and dysphoria. The Ln

50

in the following animals have been reported (all by mouth): 40 milligrams/kg (mouse) 22 milligrams/kg (rat) 17 milligrams/kg (guinea pig)

Dr. Albert R. Sperling and Mr. Joseph E. Kales, analysts in the laboratories, use the following screening tests: 1.

With both Marquis and Frohde reagents JB-336 first gives a rustorange color, which changes to a distinctive blue, somewhat like the color of washable blue ink.

2.

When heated in a concentrated sulfuric acid, JB-336 dissolves, turning the solution to a red color. This color change occurs with all esters of benzilic acid, such as Benactyzine, JB-318, and JB-336.

CAUTION: Use of this publication should be restricted to forensic

analysts or others having a legitimate need for this material.

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- 2 Ultra~violet

and infra-red spectra are attached.

"Hog" We recently received two capsules, each from a different source. One capsule contained wh:l. te powder, tht:;; other contained orange powder. Both capsules were alleged to be the "new" drug "Hog". The laboratory found them to contain phencyclidine HCL · (See Microgram No. 3) LSD Tablets We .are. still finding the· blue LSD tablets mentioned in the las.t .issue of Microgram. The tablets in the most recent evidence examined 1t1.•ere either made some time ago, or else the punch on which they were made has heen re-surfaced. ·rhe men in the microanalytical group made the latest·identificatlon from known marks on the sides of the tablets. S'l'P tablets STP tablets, also mentioned in the last issue, are still appearing. The latest evidence consisted of tablets of solid orange color. Essentially, the date remains as reported last month. In addition, the bevel angle is approximately 30 degrees, with bevel.cuts longer on one surface. A large amount of lactose is found., but no starch. These tablets have been obtained on both Coasts, and all appear to be made on a multiple punch press. These t.,Jhlets are being sold as "Syndicate Acid" in some areas. Police Chemist Seminar The fourth crime laboratory chemist 1 s school ended June 21. Students came from the States of Connecticut, Texas, Georgia, Pennsylvania, Colorado, Wisconsin, New York, New Jersey, Missouri, and Montana. Future seminars are following dates:

tentative!~

planned at Washinf:'§ton, D.C. for the

September 9-13 October 28 - November 1 March 24-29, 1969 May 5-9' 1969

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- 3 -

A regional is being planned-also tentative-for San Francisco, January 13-17, 1969. We emphasize that these are tentative schedules only. Information about these schoolR has appeared in previous issues of Microgram, and Issue No. 4 has an application blank attached. Publications of Interest 1)

"Systemic Identification of Psychotropic Drugs by tography." (J. Chrom. 1! (1967) 405-419).

Thin-l~ayer

Chroma-

Miss Ina Zingales, Research La bora tory, Cleveland State Hosp:l.tal, Cleveland, Ohio, reports quick identification by combining chromogenic behavior with chromatographic comportment in two selected systems. Investigation was on a group of 45 psychotropic drugs having different chemical compositions and pharmacological activity~ The procedure is based on the compounds chromogenic behavior in respect to Folin-Ciocalteau reagent. 2)

Mr. Thomas G. Alexander, Bureau of Science, u.s. Food and Drug tells us that AOAC infra-red and ultra-violet spectra catalogs of compounds of pharmaceutical interest appear in the Journal. of the Association of Official Analytical Chemists as follows:

Administratio~,

First Publication: Supplement I Supplement II

Vol. 45, p. 797-900 Vol. 47, p. 918-941 Vol. 49, p. 1109-1153

(1962) (1964) (1966)

The cost of these publications are $2.00, $1.00, and $1.00, respectively, or $3.50 for the complete series. (Add $.50 for foreign postage.) Order from:

3)

Association of Official Analytical Chemists Box 540 Benjamin Franklin Station Washington, D.C. 20044

"Applications of Thin-Layer Chromatography in Pharmaceutical Analysis". (J. Pharm. Sci. 56 (1967) 413-436) by J. P. Comer and I. Comer. A review article and guide to the literature on TLC of drugs. Includes tables of data showing aQsorbants, solvent systems, and Rf

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.. 4 Publications of Interest (cont.) values for most classes of drugs. These include TLC tables for opium, Rauwolfia, Tropane, and. other alkaloids; Analgesic-anti~ pyretics; antihistamines, barbiturates; central· stimulants; psycJ:u)t:ropic drugs; e~cipients; and others. The references l.ist 255 papers.

4)

ETHNOPHARMACOLOGIC Search for Psychoactive Drugs, Efron, Daniel H.; Holmstedt Bo; and Kline, ~athan S., editbrs Proceeding's 'of a' symposium held in San Francisco, California, January 28-30, 1967, sponsored by the Pharmacology Section, Psychopharmac,ology.Research Branch, National Institute of Mental Health,, USPH~~

Order' Publi.c, Health. Service Publication No. 1645 from the Superintendent of Documents, u.s. Government Printing Office, Washington.~ D~9:

1 20402.

Price~

$4.00 '.,.·

~

,:

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-5AS WE GO TO PRESS - NEW DIRECTOR

fi~MED:

John Edward Ingersoll, 38, ~o1as appointed Director of the Bureau of Narcotics and Dangerous Drugs by Attorney General Ra~sey Clark on July 12, ~968. Mr. Ingersoll was brrn in California. He served in counter-intelligence i.n thr, . i\rmy; earned a Bachelor of Arts in Criminology at the Univers1.tf of California at Berkeley, where he also completed two yr.n:s graduate work in public administration. He joiner~ ... he Oakland, California pollee department in 1957, where he seri!ild as a patrolman, investigator, supervisor. chief's aide and. ,,. finally .. Director of Planning and Rese'arch; In July 1961, Mr. Ingersoll was appointed Director of Field Services of the International Association of Chiefs of Police. Working out of Washingto:t, D.C., he headed surveys and other assistance projects for law enforcement agencies throughout the nation, He was nam~d Chief of Police in Charlotte, North Carolina, July 1966, and on April 15, 1968, was appointed AssistantDirector of the Office of Law Enforcement Assistance of the Department of Justice. Mr. Ingersoll was awarded a Silver Medallion in January by the National Co;.1.ference of Chri.stians and .Jews for his work in human relations. He has contributed numerous papers oa law enforcement to professio::tal and civi'C groups, and was a lecturer at the University of California and Oakland City College. He is a past secretary-treasurer of Lam da Alpha Epsilon, a law enforcement fraternity. His many community activities have included work 0:.1. behalf of the Boy Scouts, Red Cross, and Travelers Aid Society.

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From the Archive Library of Erowid Center http://erowid.org/library/periodicals/microgram

acid

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(2)

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-20Table 1. Wavelength,

Solvent

Ultraviolet and absorptivity data for pharmaceuticals (cont'd.) Wavelength,

Dru

285

H

Anileridine

285

E

Codeine

253

Sol~

vent

Ref.

Dru

(4)

291

F

Pyridoxine HCl

(11)

291, 239

J

Acetazolamide

285

I

Codeine

(11)

291, 261

E

Veratrine

285

L

Codeine

50

(2)

292

J

Ch lorothiaz ide

285

M

Codeine

58

(4)

292

285 285

L

Codeine sulfate

40

(2)

E

Diacetylmorphine (heroin)

Ref.

430

(2) (3) (1)

430

Dihydrohydroxymorphinone

(2) (11)

( 1)

292

I

Dihydromorphinone

(11)

E

dl-Methadone

(11)

285

H

Ergonovine

(4)

292 292

Q

Methadone HCl

285

B

Ethylmorphine

(11)

292

E

Pyridoxine HCl

422

(1)

285

E

Ethylmorphine

(11)

292

H

~-Tubocurarine

200

(4)

285

H

Ethylmorphine HCl

49

(4)

292, 220

c

Acetyl sulfisoxazole

285

M

Ethylmorphine HCl

59

(4)

292, 241

H

Acetazolamide

285

I

Ethylmorphine

(11)

293

H

Methylparaben

1370

(4)

285

H

Isoproterenol

450

(4)

294

H

Chlorothiazide

444

(4)

285

B

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From the Archive Library of Erowid Center http://erowid.org/library/periodicals/microgram

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-106-

IDENTIFICATION OF SEEDS CONTAININGERGOLINEALKALOIDS BY THIN LAYERCHROMATOGRAPHY by Victor A. Folen, Forensic Chemist Special Testing and Research Laboratory Bureau of Narcotics and Dangerous Drugs

A method for the identification of ground seeds of Argyreia nervosa (small wood rose) and Ipomoea purpurea cultivars ("Pearly Gates" and "Heavenly Blue") employing thin layer chromatography is suggested as a chemical approach to the problem and as a supplement to microscopic observations. 1 ~

The advantages of the use of thin layer chromatography as a means of identifying ground seeds containing ergoline alkaloids are (1) added criteria to support microscopic observations; (2) to assist those chemists with limited botanical experience. have an almost black hull, The seeds of I. purpurea and when finely milled, are grey in color, somewhat lighter than that of ground black pepper. Fragments of the black have hulls are seen throughout. The seeds of A. nervosa a light brown parchment - like covering under which there is a fibrous layer. After grinding they are of a light brown color. Since the seeds are larger than those of I. purpurea there is less hull in relation to the endoAlso, a large number of sperm, as seen microscopically. the dissociated fibres are present in the ground material. Method: Standards

and

Sample:

For standards, I. purpur>ea cultivars are used.

and finely ground seeds of A. nervosa ("Pearly Gates" or "Heavenly Blue")

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Triturate about 200 mg of each with 5 ml. of 1% citric acid. Make basic with small additives of sodium carbo545 (acid washed), mix nate. Add 8 grams of celite thoroughly, and pack in a 25 x 300 mm chromatographic tube. Add 50 ml. of chloroform to the column and collect in a beaker. Evaporate on a steam bath to< 1 ml. and bring to volume in a 1 ml. volumetric flask. Spot 10 microliters of the standards and sample on silica gel G plates (250 microns in thickness) and develop with a chloroform - ethanol solvent system (8:2). Use a 10 cm. developing distance. After developing, compare under longwave ultraviolet light. Spray plate with p-dimethylaminobenzaldehyde reagent (2grams p-dimethylaminobenzaldehyde, 50 ml. ethanol and 50 ml. cone. hydrochloric acid). Results

and

Discussion

When the seed mixtures in citric acid were made alkaline with sodium carbonate, that of the "Heavenly Blue" turned deep reddish-brown, whereas "Pearly Gates" was a less intense greenish brown. The basic triturate of A. nervosa had the same color as that of "Pearly Gat.es". Considerable differences were found in the chromatographic patterns of A. nePvosa and I. purpurea. With "Pearly Gates" and "Heavenly Blue", similar patterns they were produced. More spots develop with A. nervosa; are of much greater intensity and there are pronounced differences in the intensities of the various spots. The spots from I. purpurea, on the other hand, are all of roughly equal intensity. These findings are in accord with those of Hylin and Watson (1) who compared quantitatively certain alkaloids from A. nervosa, "Pearly Gates" and "Heavenly Blue" and found much more alkaloidal material in A. nervosa, present in differing porportions as compared to the varieties of

I.

purpurea.

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Because of the marked differences in the patterns, it is probable that variations caused by differing geographical and environmental conditions could not alter the content of ergoline alkaloids to the extent where the chromatographic patterns of the seed extracts would be indistinguishable. Chromatographic columns were resorted to since extraction with chloroform in separators resulted in the formation of emulsions which were difficult to resolve. McJunkins, et. al. (2) have used thin ·layer chromatography to assist in the identification of A. nervosa, using different extraction procedures and T.L.C. solvent systems. Several systems have been used for the study of (3,4,5), the alkaloidal content of A. nePvosa and I. purpurea the best of which chloroform-ethanol (8:2) (5) provided separation with the method of extraction described above.

REFERENCES 1. 2.

3.

J. W. Hylin, D. P. Watson, Science 148, 499 (1965). D.~ Dillon, J. S. P. McJunkins, J. I. Thornton, Forensic Sci. Soc. 8, 121 (1968). W. A. Taber, L. C. Vining, R. A. Heacock, Phytochemistry 2,

4.

5,

65 (1965). J. Chromatog

K. Genest, M. Klavehn

19, 531 (1965).

and H. Rachelmeyer,

Deut.

101, 477 (1961).

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Apotheker

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(:onditions of Title26-INTERNAL REVENUE§ 151.424 Class "X" products.

Chapter I-Internal Revenue Service, Department of the Treasury [Treasury

Decision

7017]

PART 151-REGULATORY TAXES ON .NARCOTIC DRUGS Excepted Narcotic Pharmaceutical Preparations On September 10, 1969, a notice was published in the FEDERALREGISTER(34 F.R. 14224l stating that the Director, Bureau of Narcotics and Dangerous Drugs, pursuant to the provisions of section 4702(a) of the Internal Revenue Code of 1954, as amended by section 4(c) of the Narcotics Manufacturing Act of 1960