Ecstasy haptens and immunogens

1. A compound of the formula:

wherein:

R 19 is lower alkyl or is taken together with R 20 to form a ring, which may be a five- or six-member ring, usually a five-member ring;

R 20 is lower alkyl, or is taken together with R 19 to form a ring as discussed above,

R 1 is H or lower alkyl,

R 2 is

(a) —(CH 2 ) a C(O)(CH 2 ) b SR 3 , wherein a is 0 to 5, b is 1 to 5 and R 3 is lower alkyl or (CH 2 ) c C(O)NR 4 R 5 wherein c is 1 to 5, R 4 is H or lower alkyl and R 5 is H, an immunogenic carrier or a label, or

(b) (A) d (Q) n wherein Q is H or —(CH 2 ) e CH(R 8 )(CH 2 ) f OC(O)(CH 2 ) g R 9 being H only when d is 1 wherein A is —C(O)(CH 2 ) h C(O)NR 10 ((CH 2 ) j O(CH 2 ) k O) m (CH) 2 NR 11 —, d is 0 or 1, n is 0 or 1 wherein one of d or n is 1, h is 1 to 5, R 10 is H or lower alkyl, j is 1 to 5, k is 1 to 5, m is 1 to 3, R 11 is H or lower alkyl, e is 1 to 5, R 8 is OH or H, f is 1 to 5, g is 0 to 5, and R 9 is H, an immunogenic carrier or a label;

W is H or JR 14 being H when R 2 is other than H or lower alkyl, wherein

J is O or S,

R 14 is H, lower alkyl, a protecting group, or —(CH 2 ) r C(O)NR 15 (CH 2 ) s (D) t R 16 , wherein r is 1 to 5, R 15 is H or lower alkyl, s is 1 to 5, D is S, O, or NH, t is 0 or 1 being 0 when R 16 is maleimidyl or succinimidyl, R 16 is H, maleimidyl, succinimidyl, or —(CH 2 ) q C(O)NR 17 R 18 ,

q is 1 to 5,

R 17 is H or lower alkyl,

R 18 is H, lower alkyl, an immunogenic carrier or label,

and including the acid salts thereof.

2. A compound according to claim 1 wherein R 1 is H.

3. A compound according to claim 1 wherein R 16 is —(CH 2 ) q C(O)NR 17 R 18 and R 18 is a poly(amino acid).

4. A compound according to claim 1 wherein R 1 is H or lower alkyl, W is H and R 2 is —(CH 2 ) a C(O)(CH 2 ) b SR 3 , wherein R 3 is —(CH 2 ) c C(O)NR 4 R 5 wherein R 4 is H or lower alkyl and R 5 is a poly(amino acid).

5. A compound according to claim 1 wherein R 1 is H or lower alkyl, W is H and R 2 is —(CH 2 ) a C(O)(CH 2 ) b SR 3 , wherein R 3 is —(CH 2 ) c C(O)NR 4 R 5 wherein R 4 is H or lower alkyl and R 5 is an immunogenic carrier.

6. A compound according to claim 1 wherein R 1 is H or lower alkyl, W is H and R 2 is (A) d (Q) n wherein d is 0, n is 1, Q is —(CH 2 ) e CH(R 8 )(CH 2 ) f OC(O)(CH 2 ) g R 9 and R 9 is a poly(amino) acid.

7. A compound according to claim 1 wherein R 1 is H or lower alkyl, W is H and R 2 is (A) d (Q) n wherein d is 1, n is 1, Q is —(CH 2 ) e CH(R 8 )(CH 2 ) f OC(O)(CH 2 ) g R 9 and A is —C(O)(CH 2 ) h C(O)NR 10 ((CH 2 ) j O(CH 2 ) k O) m (CH) 2 NR 11 —, and R 9 is a poly(amino) acid.

8. A compound of the formula:

wherein:

R 1 ′ is H, lower alkyl or a protecting group,

R 2 ′ is

(a) —(CH 2 ) a C(O)(CH 2 ) b SR 3 ′, wherein a is 0 to 5, b is 1 to 5 and R 3 ′ is lower alkyl or (CH 2 ) c C(O)NR 4 ′R 5 ′ wherein c is 1 to 5, R 4 ′ is H or lower alkyl and R 5 ′ is H, an immunogenic carrier or a label, or

(b) (A) d (Q) n wherein Q is H or —(CH 2 ) e CH(R 8 ′)(CH 2 ) f OC(O)(CH 2 ) g R 9 ′ being H only when d is 1 wherein A is —C(O)(CH 2 ) h C(O)N(R 10 )((CH 2 ) j O(CH 2 ) k O) m (CH) 2 NR 11 —, d is 0 or 1, n is 0 or 1 wherein one of d or n is 1, h is 1 to 5, R 10 is H or lower alkyl, j is 1 to 5, k is 1 to 5, m is 1 to 3, R 11 is H or lower alkyl, e is 1 to 5, R 8 ′ is OH or H, f is 1 to 5, g is 0 to 5, and R 9 ′ is H, an immunogenic carrier or a label,

and including the acid salts thereof.

9. A compound according to claim 8 wherein R 1 ′ is H or lower alkyl and R 2 ′ is (—CH 2 ) a C(O)(CH 2 ) b SR 3 ′ wherein a is 0, b is 1.

10. A compound according to claim 8 wherein R 1 ′ is H or lower alkyl and R 2 ′ is —(CH 2 ) a C(O)(CH 2 ) b SR 3 ′ wherein a is 0, b is 1, R 3 ′ is (CH 2 ) c C(O)NR 4 ′R 5 ′ wherein c is 1, R 4 ′ is H and R 5 ′ is a poly(amino) acid.

11. A compound according to claim 10 wherein said poly(amino) acid is an enzyme or an immunogenic carrier.

12. A compound according to claim 8 wherein R 1 ′ is H or lower alkyl and R 2 ′ is —(CH 2 ) a C(O)(CH 2 ) b SR 3 ′ wherein a is 0, b is 1, R 3 ′ is (CH 2 ) c C(O)NR 4 ′R 5 ′ wherein c is 1, R 4 ′ is H and R 5 ′ is an immunogenic carrier.

13. A compound according to claim 8 wherein R 1 ′ is H or lower alkyl and R 2 ′ is —(CH 2 ) a C(O)(CH 2 ) b SR 3 ′ wherein a is 0, b is 1, R 3 ′ is (CH 2 ) c C(O)NR 4 ′R 5 ′ wherein c is 1, R 4 ′ is H and R 5 ′ is a particle label or a particle immunogenic carrier.

14. A compound according to claim 8 wherein R 1 ′ is H or lower alkyl and R 2 ′ is (A) d (Q) n wherein d is 0, n is 1, Q is —(CH 2 ) e CH(R 8 ′)(CH 2 ) f OC(O)(CH 2 ) g R 9 ′, e is 1, R 8 ′ is OH, f is 1, g is 0 and R 9 ′ is a poly(amino) acid.

15. A compound according to claim 14 wherein said poly(amino) acid is an enzyme or an immunogenic carrier.

16. A compound according to claim 8 wherein R 1 ′ is H or lower alkyl and R 2 ′ is (A) d (Q) n wherein d is 0, n is 1, Q is H, A is —C(O)(CH 2 ) h C(O)NR 10 ((CH 2 ) j O(CH 2 ) k O) m (CH) 2 NR 11 —, R 10′ is H, h is 2, m is 1, j is 2, k is 2, R 10′ is H.

17. A compound according to claim 8 wherein R 1 ′ is H or lower alkyl and R 2 ′ is (A) d (Q) n wherein d is 1, n is 1, Q is —(CH 2 ) e CH(R 8 ′)(CH 2 ) f OC(O)(CH 2 ) g R 9 ′, e is 1, R 8′ is OH, f is 1, g is 0, A is —C(O)(CH 2 ) h C(O)NR 10 ((CH 2 ) j O(CH 2 ) k O) m (CH) 2 NR 11 —, R 10′ is H, h is 2, m is 1, j is 2, R 10′ H and R 9 ′ is a poly(amino) acid or a particle label or a particle immunogenic carrier.

18. A compound according to claim 17 wherein R 9 ′ is a poly(amino) acid, which is an enzyme or an immunogenic carrier.

19. A compound according to claim 17 wherein R 9 ′ is a particle label or a particle immunogenic carrier.

20. A compound of the formula:

wherein:

R 12 ′ is H or lower alkyl,

R 13 ′ is H or lower alkyl,

R 14 ′ is a protecting group, or —(CH 2 ) r C(O)NR 15 ′(CH 2 ) s (D) t R 16 ′, wherein r is 1 to 5, R 15 ′ is H or lower alkyl, s is 1 to 5, D is S, O, or NH, t is 0 or 1 being 0 when R 16 ′ is maleimidyl or succinimidyl, R 16 ′ is H, a protecting group, maleimidyl or succinimidyl, or —(CH 2 ) q C(O)NR 17 ′R 18 ′ wherein q is 1 to 5,

R 17 ′ is H, lower alkyl or a protecting group,

R 18 ′ is H, lower alkyl, a protecting group, an immunogenic carrier or a label,

and including the acid salts thereof.

21. A compound according to claim 20 wherein R 12′ is H and R 13′ is H or lower alkyl, R 14 ′ is —(CH 2 ) r C(O)NR 15 ′(CH 2 ) s (D) t R 16 ′, wherein r is 1, R 15 ′ is H, s is 2, D is S, t is 1 and R 16 ′ is H.

22. A compound according to claim 20 wherein R 12′ is H and R 13′ is H or lower alkyl, R 14 ′ is —(CH 2 ) r C(O)NR 15 ′(CH 2 ) s (D) t R 16 ′, wherein r is 1, R 15 ′ is H, s is 2, t is 0 and R 16 ′ is succinimidyl or maleimidyl.

23. A compound according to claim 20 wherein R 12′ is H and R 13′ is H or lower alkyl, R 14 ′ is —(CH 2 ) r C(O)NR 15 ′(CH 2 ) s (D) t R 16 ′, wherein r is 1, R 15 ′ is H, s is 2, D is S, t is 1 and R 16 ′ is —(CH 2 ) q C(O)NR 17 ′R 18 ′, q is 1, R 17 ′ is H and R 18 ′ is a poly(amino) acid or a particle label or a particle immunogenic carrier.

24. A compound according to claim 23 wherein R 18 ′ is a particle label or a particle immunogenic carrier.

25. An antibody raised against a compound according to claim 15 wherein said poly(amino) acid is an immunogenic carrier.

26. An antibody raised against a compound according to claim 18 wherein said poly(amino) acid is an immunogenic carrier.

27. An antibody raised against a compound according to claim 23 wherein R 17 ′ is a poly(amino) acid, which is an immunogenic carrier.

28. A reagent system comprising a compound according to claim 15 wherein said poly(amino) acid is an enzyme, an antibody for methylenedioxyamphetamine and/or an antibody for methylenedioxymethamphetamine and/or an antibody for methylenedioxyethamphetamine.

29. A reagent system comprising a compound according to claim 18 wherein said poly(amino) acid is an enzyme, an antibody for methylenedioxyamphetamine and/or an antibody for methylenedioxymethamphetamine and/or an antibody for methylenedioxyethamphetamine.

30. A reagent system comprising a compound according to claim 23 wherein R 17 ′ is a poly(amino) acid, which is an enzyme, an antibody for methylenedioxyamphetamine and/or an antibody for methylenedioxymethamphetamine and/or an antibody for methylenedioxyethamphetamine.

31. A method for determining methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in a sample suspected of containing methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine, said method comprising:

(a) providing in combination in a medium:

(i) said sample and

(ii) a reagent system according to claim 28 ; and

(b) examining said medium for the presence of a complex comprising said methylenedioxyamphetamine and said antibody for methylenedioxyamphetamine and/or a complex of said methylenedioxymethamphetamine and said antibody for methylenedioxymethamphetamine, the presence thereof indicating the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in said sample.

32. A method according to claim 31 wherein said examining comprises measuring signal from said enzyme, the amount thereof being related to the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in said sample.

33. A method according to claim 32 wherein said method is a homogeneous method and said medium is examined for the amount of said signal.

34. A method according to claim 32 wherein said method is a heterogeneous method and said complex, if present, is separated from said medium and said medium or said complex is examined for the amount of said signal.

35. A method for determining methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in a sample suspected of containing methylenedioxyamphetamine and/or methylenedioxy-methamphetamine and/or methylenedioxyethamphetamine, said method comprising:

(a) providing in combination in a medium:

(i) said sample and

(ii) a reagent system according to claim 29 ; and

(b) examining said medium for the presence of a complex comprising said methylenedioxyamphetamine and said antibody for methylenedioxyamphetamine and/or a complex of said methylenedioxymethamphetamine and said antibody for methylenedioxymethamphetamine and/or a complex of said methylenedioxyethamphetamine and said antibody for methylenedioxyethamphetamine, the presence thereof indicating the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in said sample.

36. A method according to claim 35 wherein said examining comprises measuring signal from said enzyme, the amount thereof being related to the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylene dioxyethamphetamine in said sample.

37. A method according to claim 36 wherein said method is a homogeneous method and said medium is examined for the amount of said signal.

38. A method according to claim 36 wherein said method is a heterogeneous method and said complex, if present, is separated from said medium and said medium or said complex is examined for the amount of said signal.

39. A method for determining methylenedioxyamphetamine and/or methylenedioxymethamphetamine in a sample suspected of containing methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylene dioxyethamphetamine, said method comprising:

(a) providing in combination in a medium:

(i) said sample and

(ii) a reagent system according to claim 30 ; and

(b) examining said medium for the presence of a complex comprising said methylenedioxyamphetamine and said antibody for methylenedioxyamphetamine and/or a complex of said methylenedioxymethamphetamine and said antibody for methylenedioxymethamphetamine and/or a complex of said methylenedioxymethamphetamine and said antibody for methylenedioxymethamphetamine, the presence thereof indicating the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine in said sample.

40. A method according to claim 39 wherein said examining comprises measuring signal from said enzyme, the amount thereof being related to the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylene dioxyethamphetamine in said sample.

41. A method according to claim 40 wherein said method is a homogeneous method and said medium is examined for the amount of said signal.

42. A method according to claim 40 wherein said method is a heterogeneous method and said complex, if present, is separated from said medium and said medium or said complex is examined for the amount of said signal.

43. A method for determining amphetamine and/or methamphetamine and/or methylenedioxyethamphetamine in a sample suspected of containing methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylene dioxyethamphetamine, said method comprising:

(a) providing in combination in a medium:

(i) said sample,

(ii) an antibody for methylenedioxyamphetamine, and/or

(iii) an antibody for methylenedioxymethamphetamine, and/or

(iv) an antibody for methylenedioxyethamphetamine, and

(v) a compound of the formula:

 wherein:

R 1 ′ is H,

R 2 ′ is H, methyl or ethyl,

r′ is 1 to 5,

s′ is 1 to 5,

q′ is 1 to 5,

Z′ is an enzyme,

n′ is an integer between 1 and the molecular weight of said enzyme divided by about 500; and

(b) examining said medium for the presence of a complex comprising said methylenedioxyamphetamine and said antibody for methylenedioxyamphetamine and/or a complex of said methylenedioxymethamphetamine and said antibody for methylenedioxymethamphetamine and/or a complex of said methylenedioxyethamphetamine and said antibody for methylenedioxyethamphetamine, the presence thereof indicating the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in said sample.

44. A method according to claim 43 wherein said examining comprises measuring signal from said enzyme, the amount thereof being related to the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylene-dioxyethamphetamine in said sample.

45. A method according to claim 44 wherein said method is a homogeneous method and said medium is examined for the amount of said signal.

46. A method according to claim 44 wherein said method is a heterogeneous method and said complex, if present, is separated from said medium and said medium or said complex is examined for the amount of said signal.

47. A method according to claim 43 wherein said enzyme is glucose-6-phosphate dehydrogenase.

48. A method for determining methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in a sample suspected of containing methylenedioxyamphetamine and/or methylenedioxy-methamphetamine and/or methylenedioxyethamphetamine, said method comprising:

(a) providing in combination in a medium:

(i) said sample,

(ii) an antibody for methylenedioxyamphetamine, and/or

(iii) an antibody for methylenedioxymethamphetamine, and/or

(iv) an antibody for methylenedioxyethamphetamine, and

(v) a compound of the formula:

 wherein:

R 1 ′ is H, or methyl, or ethyl,

a′ is 1 to 5,

y′ is 1,

Z′ is an enzyme,

c′ is 1 to 5,

n′ is an integer between 1 and the molecular weight of said enzyme divided by about 500; and

(b) examining said medium for the presence of a complex comprising said methylenedioxyamphetamine and said antibody for methylenedioxyamphetamine and/or a complex of said methylenedioxymethamphetamine and said antibody for methylenedioxymethamphetamine and/or a complex of said methylenedioxyethamphetamine and said antibody for methylenedioxyethamphetamine, the presence thereof indicating the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxymethamphetamine in said sample.

49. A method according to claim 48 wherein said examining comprises measuring signal from said enzyme, the amount thereof being related to the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in said sample.

50. A method according to claim 49 wherein said method is a homogeneous method and said medium is examined for the amount of said signal.

51. A method according to claim 49 wherein said method is a heterogeneous method and said complex, if present, is separated from said medium and said medium or said complex is examined for the amount of said signal.

52. A method according to claim 48 wherein said enzyme is glucose-6-phosphate dehydrogenase.

53. A method for determining methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in a sample suspected of containing methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine, said method comprising:

(a) providing in combination in a medium:

(i) said sample,

(ii) conjugate of an enzyme and a methylenedioxyamphetamine analog and/or a conjugate of an enzyme and a methylenedioxymethamphetamine analog and/or a conjugate of an enzyme and a methylenedioxyethamphetamine analog,

(i) an antibody for methylenedioxyamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is H,

R 2 ′ is H,

r′ is 1 to 5,

s′ is 1 to 5,

q′ is 1 to 5,

Z′ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500; and/or

(iv) an antibody for methylenedioxymethamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is H,

R 2 ′ is methyl,

r′ is 1 to 5,

s′ is 1 to 5,

q′ is 1 to 5,

Z′ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500; and/or

(v) an antibody for methylenedioxyethamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is H,

R 2 ′ is ethyl,

r′ is 1 to 5,

s′ is 1 to 5,

q′ is 1 to 5,

Z′ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500; and

(b) examining said medium for the presence of a complex comprising said methylenedioxyamphetamine and said antibody for methylenedioxyamphetamine and/or a complex of said methylenedioxymethamphetamine and said antibody for methylenedioxymethamphetamine and/or a complex of said methylenedioxyethamphetamine and said antibody for methylenedioxyethamphetamine, the presence thereof indicating the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in said sample.

54. A method according to claim 53 wherein said examining comprises measuring signal from said enzyme, the amount thereof being related to the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in said sample.

55. A method according to claim 54 wherein said method is a homogeneous method and said medium is examined for the amount of said signal.

56. A method according to claim 54 wherein said method is a heterogeneous method and said complex, if present, is separated from said medium and said medium or said complex is examined for the amount of said signal.

57. A method according to claim 54 wherein said enzyme is glucose-6-phosphate dehydrogenase.

58. A method for determining methylenedioxyamphetamine and/or methylenedioxymethamphetamine in a sample suspected of containing methylenedioxyamphetamine and/or methylenedioxymethamphetamine, said method comprising:

(a) providing in combination in a medium:

(i) said sample,

(ii) a conjugate of an enzyme and an methylenedioxyamphetamine analog and/or a conjugate of an enzyme and a methylenedioxymethamphetamine analog and/or a conjugate of an enzyme and a methylenedioxyethamphetamine analog,

(i) an antibody for methylenedioxyamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is H,

a′ is 1 to 5,

y′ is 1,

Z″ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

c′ is 1 to 5,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500; and/or

(iv) an antibody for methylenedioxymethamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is methyl,

a′ is 1 to 5,

y′ is 1,

Z″ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

c′ is 1 to 5,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500; and/or

(v) an antibody for methylenedioxyethamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is ethyl,

a′ is 1 to 5,

y′ is 1,

Z″ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

c′ is 1 to 5,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500; and

(b) examining said medium for the presence of a complex comprising said methylenedioxyamphetamine and said antibody for methylenedioxyamphetamine and/or a complex of said methylenedioxymethamphetamine and said antibody for methylenedioxymethamphetamine and/or a complex of said methylenedioxyethamphetamine and said antibody for methylenedioxyethamphetamine, the presence thereof indicating the presence of said amphetamine and/or methamphetamine and/or methylenedioxyethamphetamine in said sample.

59. A method according to claim 58 wherein said examining comprises measuring signal from said enzyme, the amount thereof being related to the presence of said methylenedioxyamphetamine and/or methylenedioxymethamphetamine and/or methylenedioxyethamphetamine in said sample.

60. A method according to claim 59 wherein said method is a homogeneous method and said medium is examined for the amount of said signal.

61. A method according to claim 59 wherein said method is a heterogeneous method and said complex, if present, is separated from said medium and said medium or said complex is examined for the amount of said signal.

62. A method according to claim 58 wherein said enzyme is glucose-6-phosphate dehydrogenase.

63. A kit comprising in packaged combination:

(i) an antibody for methylenedioxyamphetamine, and/or

(ii) an antibody for methylenedioxymethamphetamine, and/or

(iii) an antibody for methylenedioxyethamphetamine, and

(iv) a compound of the formula:

 wherein:

R 1 ′ is H,

R 2 ′ is H, methyl, or ethyl,

r′ is 1 to 5,

s′ is 1 to 5,

q′ is 1 to 5,

Z′ is an enzyme such as, for example, glucose-6-phosphate dehydrogenase,

n′ is an integer between 1 and the molecular weight of said enzyme divided by about 500.

64. A kit according to claim 63 wherein said enzyme is glucose-6-phosphate dehydrogenase.

65. A kit comprising in packaged combination:

(i) an antibody for methylenedioxyamphetamine,

(ii) an antibody for methylenedioxymethamphetamine, and/or

(iii) an antibody for methylenedioxyethamphetamine, and

(iv) a compound of the formula:

 wherein:

R 1 ′ is H, methyl or ethyl,

a′ is 1 to 5, usually 1,

y′ is 1,

Z′ is an enzyme such as, for example, glucose-6-phosphate dehydrogenase,

c′ is 1 to 5,

n′ is an integer between 1 and the molecular weight of said enzyme divided by about 500.

66. A kit according to claim 65 wherein said enzyme is glucose-6-phosphate dehydrogenase.

67. A kit comprising in packaged combination:

(i) a conjugate of an enzyme and a methylenedioxyamphetamine analog and/or a conjugate of an enzyme and a methylenedioxymethamphetamine analog, and/or a conjugate of an enzyme and a methylenedioxyethamphetamine analog; and

(ii) an antibody for methylenedioxyamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is H,

R 2 ′ is H,

r′ is 1 to 5,

s′ is 1 to 5,

q′ is 1 to 5,

Z′ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500; and/or

(iii) an antibody for methylenedioxymethamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is H,

R 2 ′ is methyl,

r′ is 1 to 5,

s′ is 1 to 5,

q′ is 1 to 5,

Z′ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500, and/or

(iv) an antibody for methylenedioxyethamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is H,

R 2 ′ is ethyl,

r′ is 1 to 5,

s′ is 1 to 5,

q′ is 1 to 5,

Z′ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500.

68. A kit comprising in packaged combination:

(i) a conjugate of an enzyme and an methylenedioxyamphetamine analog and/or a conjugate of an enzyme and a methylenedioxymethamphetamine analog, and

(ii) an antibody for methylenedioxyamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is H,

a′ is 1 to 5,

y′ is 1,

Z″ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

c′ is 1 to 5,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500; and/or

(iii) an antibody for methylenedioxymethamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is methyl,

a′ is 1 to 5,

y′ is 1,

Z″ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

c′ is 1 to 5,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500, and/or

(iv) an antibody for methylenedioxyethamphetamine, said antibody being raised against a compound of the formula:

 wherein:

R 1 ′ is ethyl,

a′ is 1 to 5,

y′ is 1,

Z″ is an immunogenic protein or a non-poly(amino acid) immunogenic carrier,

c′ is 1 to 5,

n″ is an integer between 1 and the molecular weight of said immunogenic protein or said immunogenic carrier divided by about 500.