diff --git a/llvm/lib/Target/X86/X86ISelLowering.cpp b/llvm/lib/Target/X86/X86ISelLowering.cpp
index 8c531f421799..ee6a14cdb01e 100644
--- a/llvm/lib/Target/X86/X86ISelLowering.cpp
+++ b/llvm/lib/Target/X86/X86ISelLowering.cpp
@@ -30256,22 +30256,37 @@ static SDValue combineMul(SDNode *N, SelectionDAG &DAG,
   }
 
   if (!NewMul) {
-    assert(MulAmt != 0 && MulAmt != (VT == MVT::i64 ? UINT64_MAX : UINT32_MAX)
-           && "Both cases that could cause potential overflows should have "
-              "already been handled.");
-    if (isPowerOf2_64(MulAmt - 1))
-      // (mul x, 2^N + 1) => (add (shl x, N), x)
-      NewMul = DAG.getNode(ISD::ADD, DL, VT, N->getOperand(0),
-                                DAG.getNode(ISD::SHL, DL, VT, N->getOperand(0),
-                                DAG.getConstant(Log2_64(MulAmt - 1), DL,
-                                MVT::i8)));
-
-    else if (isPowerOf2_64(MulAmt + 1))
-      // (mul x, 2^N - 1) => (sub (shl x, N), x)
-      NewMul = DAG.getNode(ISD::SUB, DL, VT, DAG.getNode(ISD::SHL, DL, VT,
-                                N->getOperand(0),
-                                DAG.getConstant(Log2_64(MulAmt + 1),
-                                DL, MVT::i8)), N->getOperand(0));
+    assert(MulAmt != 0 &&
+           MulAmt != (VT == MVT::i64 ? UINT64_MAX : UINT32_MAX) &&
+           "Both cases that could cause potential overflows should have "
+           "already been handled.");
+    int64_t SignMulAmt = C->getSExtValue();
+    if ((SignMulAmt != INT64_MIN) && (SignMulAmt != INT64_MAX) &&
+        (SignMulAmt != -INT64_MAX)) {
+      int NumSign = SignMulAmt > 0 ? 1 : -1;
+      bool IsPowerOf2_64PlusOne = isPowerOf2_64(NumSign * SignMulAmt - 1);
+      bool IsPowerOf2_64MinusOne = isPowerOf2_64(NumSign * SignMulAmt + 1);
+      if (IsPowerOf2_64PlusOne) {
+        // (mul x, 2^N + 1) => (add (shl x, N), x)
+        NewMul = DAG.getNode(
+            ISD::ADD, DL, VT, N->getOperand(0),
+            DAG.getNode(ISD::SHL, DL, VT, N->getOperand(0),
+                        DAG.getConstant(Log2_64(NumSign * SignMulAmt - 1), DL,
+                                        MVT::i8)));
+      } else if (IsPowerOf2_64MinusOne) {
+        // (mul x, 2^N - 1) => (sub (shl x, N), x)
+        NewMul = DAG.getNode(
+            ISD::SUB, DL, VT,
+            DAG.getNode(ISD::SHL, DL, VT, N->getOperand(0),
+                        DAG.getConstant(Log2_64(NumSign * SignMulAmt + 1), DL,
+                                        MVT::i8)),
+            N->getOperand(0));
+      }
+      // To negate, subtract the number from zero
+      if ((IsPowerOf2_64PlusOne || IsPowerOf2_64MinusOne) && NumSign == -1)
+        NewMul =
+            DAG.getNode(ISD::SUB, DL, VT, DAG.getConstant(0, DL, VT), NewMul);
+    }
   }
 
   if (NewMul)
diff --git a/llvm/test/CodeGen/X86/imul.ll b/llvm/test/CodeGen/X86/imul.ll
index 9d4d19332dbb..45a83cc5dfd9 100644
--- a/llvm/test/CodeGen/X86/imul.ll
+++ b/llvm/test/CodeGen/X86/imul.ll
@@ -171,3 +171,233 @@ define i64 @mul18446744073709551615_64(i64 %A) {
     %mul = mul i64 %A, 18446744073709551615
     ret i64 %mul
 }
+
+define i32 @test(i32 %a) {
+; X64-LABEL: test:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    movl %edi, %eax
+; X64-NEXT:    shll $5, %eax
+; X64-NEXT:    subl %edi, %eax
+; X64-NEXT:    retq
+;
+; X86-LABEL: test:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %ecx
+; X86-NEXT:    movl %ecx, %eax
+; X86-NEXT:    shll $5, %eax
+; X86-NEXT:    subl %ecx, %eax
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i32 %a, 31
+	ret i32 %tmp3
+}
+
+define i32 @test1(i32 %a) {
+; X64-LABEL: test1:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    movl %edi, %eax
+; X64-NEXT:    shll $5, %eax
+; X64-NEXT:    subl %edi, %eax
+; X64-NEXT:    negl %eax
+; X64-NEXT:    retq
+;
+; X86-LABEL: test1:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %ecx
+; X86-NEXT:    movl %ecx, %eax
+; X86-NEXT:    shll $5, %eax
+; X86-NEXT:    subl %ecx, %eax
+; X86-NEXT:    negl %eax
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i32 %a, -31
+	ret i32 %tmp3
+}
+
+
+define i32 @test2(i32 %a) {
+; X64-LABEL: test2:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    # kill: %EDI<def> %EDI<kill> %RDI<def>
+; X64-NEXT:    movl %edi, %eax
+; X64-NEXT:    shll $5, %eax
+; X64-NEXT:    leal (%rax,%rdi), %eax
+; X64-NEXT:    retq
+;
+; X86-LABEL: test2:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %ecx
+; X86-NEXT:    movl %ecx, %eax
+; X86-NEXT:    shll $5, %eax
+; X86-NEXT:    addl %ecx, %eax
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i32 %a, 33
+	ret i32 %tmp3
+}
+
+define i32 @test3(i32 %a) {
+; X64-LABEL: test3:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    # kill: %EDI<def> %EDI<kill> %RDI<def>
+; X64-NEXT:    movl %edi, %eax
+; X64-NEXT:    shll $5, %eax
+; X64-NEXT:    leal (%rax,%rdi), %eax
+; X64-NEXT:    negl %eax
+; X64-NEXT:    retq
+;
+; X86-LABEL: test3:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %ecx
+; X86-NEXT:    movl %ecx, %eax
+; X86-NEXT:    shll $5, %eax
+; X86-NEXT:    addl %ecx, %eax
+; X86-NEXT:    negl %eax
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i32 %a, -33
+	ret i32 %tmp3
+}
+
+define i64 @test4(i64 %a) {
+; X64-LABEL: test4:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    movq %rdi, %rax
+; X64-NEXT:    shlq $5, %rax
+; X64-NEXT:    subq %rdi, %rax
+; X64-NEXT:    retq
+;
+; X86-LABEL: test4:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %eax
+; X86-NEXT:    movl %eax, %ecx
+; X86-NEXT:    shll $5, %ecx
+; X86-NEXT:    subl %eax, %ecx
+; X86-NEXT:    movl $31, %eax
+; X86-NEXT:    mull {{[0-9]+}}(%esp)
+; X86-NEXT:    addl %ecx, %edx
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i64 %a, 31
+	ret i64 %tmp3
+}
+
+define i64 @test5(i64 %a) {
+; X64-LABEL: test5:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    movq %rdi, %rax
+; X64-NEXT:    shlq $5, %rax
+; X64-NEXT:    subq %rdi, %rax
+; X64-NEXT:    negq %rax
+; X64-NEXT:    retq
+;
+; X86-LABEL: test5:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    pushl %esi
+; X86-NEXT:  .Lcfi0:
+; X86-NEXT:    .cfi_def_cfa_offset 8
+; X86-NEXT:  .Lcfi1:
+; X86-NEXT:    .cfi_offset %esi, -8
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %ecx
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %eax
+; X86-NEXT:    movl %eax, %esi
+; X86-NEXT:    shll $5, %esi
+; X86-NEXT:    subl %eax, %esi
+; X86-NEXT:    movl $-31, %edx
+; X86-NEXT:    movl %ecx, %eax
+; X86-NEXT:    mull %edx
+; X86-NEXT:    subl %ecx, %edx
+; X86-NEXT:    subl %esi, %edx
+; X86-NEXT:    popl %esi
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i64 %a, -31
+	ret i64 %tmp3
+}
+
+
+define i64 @test6(i64 %a) {
+; X64-LABEL: test6:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    movq %rdi, %rax
+; X64-NEXT:    shlq $5, %rax
+; X64-NEXT:    leaq (%rax,%rdi), %rax
+; X64-NEXT:    retq
+;
+; X86-LABEL: test6:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %eax
+; X86-NEXT:    movl %eax, %ecx
+; X86-NEXT:    shll $5, %ecx
+; X86-NEXT:    addl %eax, %ecx
+; X86-NEXT:    movl $33, %eax
+; X86-NEXT:    mull {{[0-9]+}}(%esp)
+; X86-NEXT:    addl %ecx, %edx
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i64 %a, 33
+	ret i64 %tmp3
+}
+
+define i64 @test7(i64 %a) {
+; X64-LABEL: test7:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    movq %rdi, %rax
+; X64-NEXT:    shlq $5, %rax
+; X64-NEXT:    leaq (%rax,%rdi), %rax
+; X64-NEXT:    negq %rax
+; X64-NEXT:    retq
+;
+; X86-LABEL: test7:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    pushl %esi
+; X86-NEXT:  .Lcfi2:
+; X86-NEXT:    .cfi_def_cfa_offset 8
+; X86-NEXT:  .Lcfi3:
+; X86-NEXT:    .cfi_offset %esi, -8
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %ecx
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %eax
+; X86-NEXT:    movl %eax, %esi
+; X86-NEXT:    shll $5, %esi
+; X86-NEXT:    addl %eax, %esi
+; X86-NEXT:    movl $-33, %edx
+; X86-NEXT:    movl %ecx, %eax
+; X86-NEXT:    mull %edx
+; X86-NEXT:    subl %ecx, %edx
+; X86-NEXT:    subl %esi, %edx
+; X86-NEXT:    popl %esi
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i64 %a, -33
+	ret i64 %tmp3
+}
+
+define i64 @testOverflow(i64 %a) {
+; X64-LABEL: testOverflow:
+; X64:       # BB#0: # %entry
+; X64-NEXT:    movabsq $9223372036854775807, %rax # imm = 0x7FFFFFFFFFFFFFFF
+; X64-NEXT:    imulq %rdi, %rax
+; X64-NEXT:    retq
+;
+; X86-LABEL: testOverflow:
+; X86:       # BB#0: # %entry
+; X86-NEXT:    pushl %esi
+; X86-NEXT:  .Lcfi4:
+; X86-NEXT:    .cfi_def_cfa_offset 8
+; X86-NEXT:  .Lcfi5:
+; X86-NEXT:    .cfi_offset %esi, -8
+; X86-NEXT:    movl {{[0-9]+}}(%esp), %ecx
+; X86-NEXT:    movl $-1, %edx
+; X86-NEXT:    movl %ecx, %eax
+; X86-NEXT:    mull %edx
+; X86-NEXT:    movl %ecx, %esi
+; X86-NEXT:    shll $31, %esi
+; X86-NEXT:    subl %ecx, %esi
+; X86-NEXT:    addl %esi, %edx
+; X86-NEXT:    subl {{[0-9]+}}(%esp), %edx
+; X86-NEXT:    popl %esi
+; X86-NEXT:    retl
+entry:
+	%tmp3 = mul i64 %a, 9223372036854775807
+	ret i64 %tmp3
+}