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FACT SHEET

pCPP

September 2016

For more information, please contact: Dr. P. Blanckaert Coordinator Belgian Early Warning System Drugs Scientific Institute of Public Health National Focal Point on Drugs Jyliette Wytsmanstraat 14 B-1050 Brussels, Belgium Tel : 02/642 5408 bewsd@wiv-isp.be

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A. General information Recent collected sample in Belgium Substance: pCPP mixture with amphetamines

Date of Collection: August 2016

Date of analysis: September 2016

Color: Pink

Region: Brussels

Diameter: 8mm

Thickness: 5mm

Tablet weight: 230 mg

Created

September 2016

Updated

/

Type

Psychotropic Substances

Group

Piperazine Derivates

Name

p-Chlorophenylpiperazine (pCPP)

Nature of substance

pCPP is a piperazine-derived designer drug, which has been reported for the first time

in the Reitox Early warning system through a Reporting Form in November 2006 by

France.

Systematic chemical name

1-(4-chlorophenyl)piperazine

Other names

1-(4-chlorophenyl)piperazine is the systematic chemical name but the substance is

better known by one of its codenames pCPP (where ‘p’ stands for para, signifying the

fourth position of the chlorine atom on the phenyl ring, and ‘CPP’ stands for

chlorophenylpiperazine), 4CPP or 4Cl-PP. Depending on the position of the chlorine

atom, other possible CPP isomers are 1-(3-chlorophenyl)piperazine (for meta-

CPP) and 1-(2-chlorophenyl)piperazine, (codenames oCPP (for ortho-CPP), 2CPP or

2Cl-PP). As use of codenames could be confusing, they should be used only for initial

orientation.

B. Alerts

Alerts

The Belgian Early Warning System Drugs (BEWSD) issued an alert in september

2016 concerning a tablet containing amphetamine and pCPP.

Reports to EMCDDA

Latvia: In its EWS Report for the 1st half of 2009 the NFP reported 12 seizures

totalizing 952 tablets and 2 seizures of 3.2532g powder.

Sweden: In its EWS Report for the 1st half of 2009 the NFP reported 1 seizure of

0,73g powder; 1 seizure of 5 capsules; 25 seizures of tablets, 249 units; 4 seizures of

tablets, 497 units. (reported as mCPP or pCPP).

Switzerland: On 25 July 2009 an ecstasy tablet containing pCPP (36.24mg) and

mCPP was reported in Switzerland for the first time.

Latvia: In its EWS Report for the 1st half of 2008 the NFP reported 5 seizures of 22

tablets.

Bulgaria: In March 2007 the NFP reported 1 seizure of 49.385 g white tablets with

Rolls Royce logo seized in Asenovgrad in 2006. Tablets containing 5% MDMA.

Bulgaria: In March 2007 the NFP reported 1 seizure of 64 white tablets with

"Crocodile" logo seized in Kardzhali in 2006.

Bulgaria: In March 2007 the NFP reported 1 seizure of 1 white tablet with Rolls

Royce logo seized in Sofia in 2006. Tablet containing 6% MDMA.

Bulgaria: In March 2007 the NFP reported 1 seizure of 1 white tablet with Mitsubishi

logo seized in Varna in 2006. Tablet containing 1% MDMA and caffeine.

Bulgaria: In March 2007 the NFP reported 1 seizure of 3,55 g white tablets with

Mitsubishi logo seized in Varna in 2006. Tablets containing 27% MDMA.

Bulgaria: In March 2007 the NFP reported 1 seizure of 260 white tablets, "heart"

logo, seized in Varna in 2006. Tablets containing 1% MDMA.

Bulgaria: In March 2007 the NFP reported 1 seizure of 3 white tablets, Mitsubishi

logo seized in Sofia in 2006.

France: In November 2006 the NFP reported a collected sample of powder. It was

collected in Lyon in September and was sniffed in a party.

C. Pictures

Recent collected sample in Belgium

D. Clinical information

Usage

A number of piperazine derivatives have been reported as recreational drugs. Only

limited investigations have been conducted on the proprerties of pCPP. The isomers,

predominantly mCPP, have been used as surreptitious substitutes for MDMA.

Scientific research has demonstrated pCPP to have serotonergic effects, likely acting

as a non-selective serotonin receptor agonist and/or releasing agent.

Health risks

headache, nausea, severe halucinations, drunkenness.

following the recreational use of piperazine party drugs, users may experience periods

of exertion, lack of sleep or dehydratation.

Other uses

/

E. Legal status

Belgium: controlled as of 22 October 2006

F. Chemistry

Other chemical names and variants

Para-chlorophenylpiperazine (see also code names)

Chemical Abstracts Service (CAS) registry number

pCPP (CAS# 38212-33-8)

Molecular information

The piperazine-derived designer drugs could be divided into:

(a) benzylpiperazines – including 1-benzyl-piperazine (BZP); and 1-(3,4-

methylenedioxybenzyl)piperazine (MDBP); and

(b) phenylpiperazines – including (1-(4-methoxyphenyl)-piperazine (MeOPP); 1-(3-

trifluoromethylphenyl)-piperazine (TFMPP); 1-(3-chlorophenyl)piperazine (mCPP)

and 1-(4-chlorophenyl)piperazine (pCPP).

Molecular structure:

Molecular formula: C10H13ClN2

Molecular weight: 196.68

Identification and analytical profile

See annex: "Analytical profiles of the piperazines", from the LTG (formerly known as

the London Toxicology Group)

G. References

/

Analytical profiles of the piperazines Over the past few months (Autumn 2006) members of LTG have become aware of an increasing number of piperazine compounds sold on websites as “herbal ecstasy”. They are often promoted as a legal alternative to MDMA, sometimes as a “harm minimisation” strategy. None of the compounds are licensed medicines or have been evaluated for their safety. The health consequences of the widespread availability are beginning to emerge with reports of hospitalisations and involvement in road accidents. This monograph presents brief analytical profiles of the piperazine derivatives found in “illicit” tablets and capsules in the UK. Not all the compounds listed have been found in products but are presented because they are positional isomers of those that have. Isomers that are not resolved by GC/MS may be differentiated by HPLC with UV diode array detection because the UV absorption spectra vary. Analytical standards of all the compounds are available commercially from Sigma Aldrich, the catalogue numbers are provided in the table. Some compounds are only available as free bases, for others the hydrochloride salts are also available. Some immunoassays that target methylamfetamine also detect some of the piperazines. Dilutions of a 1mg/mL solution of the compounds in methanol were made in water for the evaluations of the immunoassay unit test devices. Thanks are due to Alan Freke of Dade Behring for donation of the Syva RapidTest d.a.u. devices.

The compounds

A 1-benzylpiperazine C11H16N2, mw 176 Sigma Aldrich 13815-25G-F

BZP

N N

B 1-(4-fluorophenyl)piperazine C10H13FN2, mw 180 Sigma Aldrich 19133-7

pFPP N N F

C

1-(3-trifluoromethylphenyl) piperazine m-trifluoromethylphenylpiperazine C11H13F3N2, mw 230 1-(α,α,α-trifluoro-m-tolyl)piperazine Sigma Aldrich T8948 (HCl)

TFMPP N N

CF3

D 1-(3-methylphenyl)piperazine C11H16N2, mw 176 Sigma Aldrich R435376 (diHCl)

mMPP N N

CH3

E 1-(4-methylphenyl)piperazine C11H16N2, mw 176 Sigma Aldrich 71868-5G-F

pMPP N N CH3

F 1-(2-chlorophenyl)piperazine C10H13ClN2, mw 196.5 Sigma Aldrich C67605 (HCl)

oCPP N N

Cl

G 1-(2-methoxyphenyl)piperazine C11H16N2O, mw 192 Sigma Aldrich M22601-5G (HCl)

oMeOPP N N

CH3O

H 1-(3-chlorophenyl)piperazine C10H13ClN2, mw 196.5 Sigma Aldrich 125180-5G (HCl)

mCPP N N

Cl

I 1-(4-methoxyphenyl)piperazine C11H16N2O, mw 192 Sigma Aldrich 571415-1G (diHCl)

pMeOPP N N OCH3

J 1-(4-chlorophenyl)piperazine C10H13ClN2, mw 196.5 Sigma Aldrich C68008

pCPP N N Cl

K 1,4-dibenzylpiperazine C18H22N2, mw 266.4 Sigma Aldrich S383937-1EA (diHCl)

DBZP N N

GC/MS Samples were analysed on a Shimadzu QP2010 gas chromatograph mass spectrometer with an HP5MS column (30m x 0.25mm, 0.50µm).

Column oven temperature 80°C

Injection temperature 225°C

Injection mode Split

Split ratio 10:1

Carrier gas Helium

Flow rate 1.0 ml/min

Pressure 9.5 psi

Ion source temperature 200°C

Interface temperature 250°C

Column oven temperature programme: Rate Final temperature Hold time

- 80°C 4 minutes

40.00°C/min 290°C 10.75 minutes

Chromatogram:-

7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.00.00

0.25

0.50

0.75

1.00

(x10,000,000)TIC

7.44

4

8.47

88.

554

8.89

88.

943

9.32

5

10.0

68

I.S I.S

(A)

(B),(C)

(D),(E)

(F),(G)

(H),(I),(J)

ID Compound Name Abbreviations Retention time (mins.)

I.S. Quinoline - 7.444

A Benzylpiperazine BZP 8.478

B 1-(4-fluorophenyl)piperazine pFPP 8.554 (front)

C m-trifluoromethylphenylpiperazine TFMPP 8.554 (tail)

D 1-(3-methylphenyl)piperazine mMPP 8.898

E 1-(4-methylphenyl)piperazine pMPP 8.898

F 1-(2-chlorophenyl)piperazine oCPP 8.943 (front)

G 1-(2-methoxyphenyl)piperazine oMeOPP 8.943 (tail)

H 1-(3-chlorophenyl)piperazine mCPP 9.325 (front)

I 1-(4-methoxyphenyl)piperazine pMeOPP 9.325

J 1-(4-chlorophenyl)piperazine pCPP 9.325

I.S. Pyribenzamine (tripelenamine) - 10.068

K 1,4-dibenzylpiperazine DBZP 10.768 (not shown)

(A) BENZYLPIPERAZINE (BZP) 8.478mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

91.1

134.1

56.1176.1

42.1 85.1 120.1207.0161.2 252.9 326.9281.0

(B) 1-(4-FLUOROPHENYL)PIPERAZINE (pFPP) 8.554mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

138.1

180.1

122.195.056.175.042.0 150.1 206.9 253.0 281.1 327.1 377.0355.2302.3

N N

N N F

(C) m-TRIFLUOROMETHYLPHENYLPIPERAZINE (TFMPP) 8.554mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

188.1

230.156.1 145.1 172.073.142.1 159.195.0 211.1127.1 252.9 327.0281.1 355.1

(D) 1-(3-METHYLPHENYL)PIPERAZINE (mMPP) 8.898mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

86.1

207.0

281.057.1 99.1 207.9 252.9135.1 326.9 387.1177.0 236.9 295.0

N N

CF3

N N

CH3

(E) 1-(4-METHYLPHENYL)PIPERAZINE (pMPP) 8.898mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

134.1

176.1

91.1 119.156.1

41.1 207.0 281.0253.0 341.1159.1

(F) 1-(2-CHLOROPHENYL)PIPERAZINE (oCPP) 8.943mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

154.1

196.156.1 138.1

77.0 111.042.1 91.0 281.1253.0207.9 327.1168.1 355.0 388.9295.1236.9

N N CH3

N N

Cl

(G) 1-(2-METHOXYPHENYL)PIPERAZINE (oMeOPP) 8.943mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

150.1

192.1135.1

120.156.177.142.1 176.1 281.0 326.9207.9 252.9 389.0

(H) 1-(3-CHLOROPHENYL)PIPERAZINE (mCPP) 9.325mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

154.1

196.073.1

56.1 138.0111.0 281.0208.095.9 252.9 327.0 355.1180.8 296.3

N N

CH3O

N N

Cl

(I) 1-(4-METHOXYPHENYL)PIPERAZINE (pMeOPP) 9.325mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

150.1

192.1

135.156.173.192.042.1 281.1207.9 253.0177.0 327.1

(J) 1-(4-CHLOROPHENYL)PIPERAZINE (pCPP) 9.325mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

154.1

196.1

56.1 138.0111.073.042.1 281.089.1 208.0 253.1 355.0327.0179.1 377.0

N N OCH3

N N Cl

(K) 1,4-DIBENZYLPIPERAZINE (DBZP) 10.768mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

91.0

175.1120.1266.2134.265.042.0 148.1 206.9 238.0 281.1 327.0 376.9354.1

N N

IMMUNOASSAY

100 micrograms / ml 10 micrograms / ml 1 microgram / ml

mAMP AMP MET mAMP MET mAMP A BZP P N N P N P B pFPP P N N P N - C TFMPP N N N N N - D mMPP P N N P N - E pMPP P N N P N - F oCPP P N ?N P ?N - G oMeOPP N N N N N - H mCPP ?P N N N N - I pMeOPP P N N P N - J pCPP P N N P N - K DBZP - - - - - -

Test Cutoff mAMP Syva RapidTest d.a.u. Methylamphetamine 1 microgram / ml AMP Syva RapidTest d.a.u. Amphetamine 1 microgram / ml MET Acon Methylamphetamine 1 microgram / ml

P positive N negative - not tested

Occurrence of the compounds in products found in UK

in UK tablets/capsules A BZP Yes B pFPP Yes C TFMPP Yes D mMPP No E pMPP No F oCPP No G oMeOPP No H mCPP Yes I pMeOPP Yes J pCPP ? K DBZP Yes

Reaction with Marquis Reagent

Marquis reagent A BZP N B pFPP N C TFMPP N D mMPP N E pMPP N F oCPP N G oMeOPP very pale pink H mCPP N I pMeOPP N J pCPP N K DBZP O

Analytical profiles of the piperazines Over the past few months (Autumn 2006) members of LTG have become aware of an increasing number of piperazine compounds sold on websites as “herbal ecstasy”. They are often promoted as a legal alternative to MDMA, sometimes as a “harm minimisation” strategy. None of the compounds are licensed medicines or have been evaluated for their safety. The health consequences of the widespread availability are beginning to emerge with reports of hospitalisations and involvement in road accidents. This monograph presents brief analytical profiles of the piperazine derivatives found in “illicit” tablets and capsules in the UK. Not all the compounds listed have been found in products but are presented because they are positional isomers of those that have. Isomers that are not resolved by GC/MS may be differentiated by HPLC with UV diode array detection because the UV absorption spectra vary. Analytical standards of all the compounds are available commercially from Sigma Aldrich, the catalogue numbers are provided in the table. Some compounds are only available as free bases, for others the hydrochloride salts are also available. Some immunoassays that target methylamfetamine also detect some of the piperazines. Dilutions of a 1mg/mL solution of the compounds in methanol were made in water for the evaluations of the immunoassay unit test devices. Thanks are due to Alan Freke of Dade Behring for donation of the Syva RapidTest d.a.u. devices.

The compounds

A 1-benzylpiperazine C11H16N2, mw 176 Sigma Aldrich 13815-25G-F

BZP

N N

B 1-(4-fluorophenyl)piperazine C10H13FN2, mw 180 Sigma Aldrich 19133-7

pFPP N N F

C

1-(3-trifluoromethylphenyl) piperazine m-trifluoromethylphenylpiperazine C11H13F3N2, mw 230 1-(α,α,α-trifluoro-m-tolyl)piperazine Sigma Aldrich T8948 (HCl)

TFMPP N N

CF3

D 1-(3-methylphenyl)piperazine C11H16N2, mw 176 Sigma Aldrich R435376 (diHCl)

mMPP N N

CH3

E 1-(4-methylphenyl)piperazine C11H16N2, mw 176 Sigma Aldrich 71868-5G-F

pMPP N N CH3

F 1-(2-chlorophenyl)piperazine C10H13ClN2, mw 196.5 Sigma Aldrich C67605 (HCl)

oCPP N N

Cl

G 1-(2-methoxyphenyl)piperazine C11H16N2O, mw 192 Sigma Aldrich M22601-5G (HCl)

oMeOPP N N

CH3O

H 1-(3-chlorophenyl)piperazine C10H13ClN2, mw 196.5 Sigma Aldrich 125180-5G (HCl)

mCPP N N

Cl

I 1-(4-methoxyphenyl)piperazine C11H16N2O, mw 192 Sigma Aldrich 571415-1G (diHCl)

pMeOPP N N OCH3

J 1-(4-chlorophenyl)piperazine C10H13ClN2, mw 196.5 Sigma Aldrich C68008

pCPP N N Cl

K 1,4-dibenzylpiperazine C18H22N2, mw 266.4 Sigma Aldrich S383937-1EA (diHCl)

DBZP N N

GC/MS Samples were analysed on a Shimadzu QP2010 gas chromatograph mass spectrometer with an HP5MS column (30m x 0.25mm, 0.50µm).

Column oven temperature 80°C

Injection temperature 225°C

Injection mode Split

Split ratio 10:1

Carrier gas Helium

Flow rate 1.0 ml/min

Pressure 9.5 psi

Ion source temperature 200°C

Interface temperature 250°C

Column oven temperature programme: Rate Final temperature Hold time

- 80°C 4 minutes

40.00°C/min 290°C 10.75 minutes

Chromatogram:-

7.0 7.5 8.0 8.5 9.0 9.5 10.0 10.5 11.00.00

0.25

0.50

0.75

1.00

(x10,000,000)TIC

7.44

4

8.47

88.

554

8.89

88.

943

9.32

5

10.0

68

I.S I.S

(A)

(B),(C)

(D),(E)

(F),(G)

(H),(I),(J)

ID Compound Name Abbreviations Retention time (mins.)

I.S. Quinoline - 7.444

A Benzylpiperazine BZP 8.478

B 1-(4-fluorophenyl)piperazine pFPP 8.554 (front)

C m-trifluoromethylphenylpiperazine TFMPP 8.554 (tail)

D 1-(3-methylphenyl)piperazine mMPP 8.898

E 1-(4-methylphenyl)piperazine pMPP 8.898

F 1-(2-chlorophenyl)piperazine oCPP 8.943 (front)

G 1-(2-methoxyphenyl)piperazine oMeOPP 8.943 (tail)

H 1-(3-chlorophenyl)piperazine mCPP 9.325 (front)

I 1-(4-methoxyphenyl)piperazine pMeOPP 9.325

J 1-(4-chlorophenyl)piperazine pCPP 9.325

I.S. Pyribenzamine (tripelenamine) - 10.068

K 1,4-dibenzylpiperazine DBZP 10.768 (not shown)

(A) BENZYLPIPERAZINE (BZP) 8.478mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

91.1

134.1

56.1176.1

42.1 85.1 120.1207.0161.2 252.9 326.9281.0

(B) 1-(4-FLUOROPHENYL)PIPERAZINE (pFPP) 8.554mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

138.1

180.1

122.195.056.175.042.0 150.1 206.9 253.0 281.1 327.1 377.0355.2302.3

N N

N N F

(C) m-TRIFLUOROMETHYLPHENYLPIPERAZINE (TFMPP) 8.554mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

188.1

230.156.1 145.1 172.073.142.1 159.195.0 211.1127.1 252.9 327.0281.1 355.1

(D) 1-(3-METHYLPHENYL)PIPERAZINE (mMPP) 8.898mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

86.1

207.0

281.057.1 99.1 207.9 252.9135.1 326.9 387.1177.0 236.9 295.0

N N

CF3

N N

CH3

(E) 1-(4-METHYLPHENYL)PIPERAZINE (pMPP) 8.898mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

134.1

176.1

91.1 119.156.1

41.1 207.0 281.0253.0 341.1159.1

(F) 1-(2-CHLOROPHENYL)PIPERAZINE (oCPP) 8.943mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

154.1

196.156.1 138.1

77.0 111.042.1 91.0 281.1253.0207.9 327.1168.1 355.0 388.9295.1236.9

N N CH3

N N

Cl

(G) 1-(2-METHOXYPHENYL)PIPERAZINE (oMeOPP) 8.943mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

150.1

192.1135.1

120.156.177.142.1 176.1 281.0 326.9207.9 252.9 389.0

(H) 1-(3-CHLOROPHENYL)PIPERAZINE (mCPP) 9.325mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

154.1

196.073.1

56.1 138.0111.0 281.0208.095.9 252.9 327.0 355.1180.8 296.3

N N

CH3O

N N

Cl

(I) 1-(4-METHOXYPHENYL)PIPERAZINE (pMeOPP) 9.325mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

150.1

192.1

135.156.173.192.042.1 281.1207.9 253.0177.0 327.1

(J) 1-(4-CHLOROPHENYL)PIPERAZINE (pCPP) 9.325mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

154.1

196.1

56.1 138.0111.073.042.1 281.089.1 208.0 253.1 355.0327.0179.1 377.0

N N OCH3

N N Cl

(K) 1,4-DIBENZYLPIPERAZINE (DBZP) 10.768mins

50 100 150 200 250 300 350 4000.0

25.0

50.0

75.0

100.0

%

91.0

175.1120.1266.2134.265.042.0 148.1 206.9 238.0 281.1 327.0 376.9354.1

N N

IMMUNOASSAY

100 micrograms / ml 10 micrograms / ml 1 microgram / ml

mAMP AMP MET mAMP MET mAMP A BZP P N N P N P B pFPP P N N P N - C TFMPP N N N N N - D mMPP P N N P N - E pMPP P N N P N - F oCPP P N ?N P ?N - G oMeOPP N N N N N - H mCPP ?P N N N N - I pMeOPP P N N P N - J pCPP P N N P N - K DBZP - - - - - -

Test Cutoff mAMP Syva RapidTest d.a.u. Methylamphetamine 1 microgram / ml AMP Syva RapidTest d.a.u. Amphetamine 1 microgram / ml MET Acon Methylamphetamine 1 microgram / ml

P positive N negative - not tested

Occurrence of the compounds in products found in UK

in UK tablets/capsules A BZP Yes B pFPP Yes C TFMPP Yes D mMPP No E pMPP No F oCPP No G oMeOPP No H mCPP Yes I pMeOPP Yes J pCPP ? K DBZP Yes

Reaction with Marquis Reagent

Marquis reagent A BZP N B pFPP N C TFMPP N D mMPP N E pMPP N F oCPP N G oMeOPP very pale pink H mCPP N I pMeOPP N J pCPP N K DBZP O